Fully Updated through Horse Ranch Pack (8/22/23)
Main Rules and Gen 1-21 Updated through Adventure Awaits (10/16/25)

Note: This is still under construction as of 8/3/2025. I will remove this notice when I’m done and update the above date.
NOTE 2: THE TRACKER IS NOW LIVE! –
https://www.simschallengetracker.com/challenges/not-so-berry-challenge-2-0

Pretty much every simmer out there has heard of the Not So Berry Challenge, even if they’re not entirely sure of what it is. At it’s heart, it’s a legacy challenge about playing a different sim with different life goals each generation. However, the Not So Berry challenge has been out for so long that there have been MANY additions to Sims 4 since it was released. Plus, I know of a lot of players who get to the end of the challenge and are so attached to their family that they don’t want to stop at ten generations. This adaptation solves that. I added in 20 more generations (as of 1/6/22) to account for the new packs, and gave each generation a color, a story and some unique goals to complete. Just for me, because apparently the challenge wasn’t hard enough already, I also added some additional (optional) goals to the first 10 generations. I tried very hard to keep the spirit of the challenge intact, and to change as little as possible for the first ten generations out of respect for the original challenge. Anyway, I hope you like this! (I, for one, have had a blast playing this rule set!)

Yes! That’s right! This whole challenge is getting a facelift! I’ve acquired a partner who is (as we speak) working on putting together a WEB-BASED free tracking system for ALL of my challenges. The Extended Not So Berry is just the first of many to be added to her website. (See the main Website News page for more info on this partnership if you’re interested!) Every Single generation here will be added to a tracking website, where you can register with a free account to track your Extended Not So Berry Challenge. And you DID read right! My ENSB is now 45 generations of drama and color-coded fun! As soon as I get it all updated and put on the website, each generation will have its own little section, split up by goal type, labelled as to what packs you need, and – the best part – LINKED to the tracking website from my partner, Calendula Petals.

Not only that, but these pages are going to change fairly heavily in looks, as well. I’m calling this new version a full 2.0, after all.

(more…)

Just a notice saying I’ve posted a new challenge that I will be playing on stream starting tomorrow. It’s called the Winchester Mystery House Challenge, and it’s a “short” build and game play challenge based on a REAL LIFE haunted house. Anyway, the challenge is now linked from the above menus and below.

Winchester Mystery House Challenge

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Updated: 1/16/25

Once you’re ready to play, grab a copy of my Timeline Adventure Challenge Tracking Spreadsheet to track your progress!

Note on Lots: I will be building pre-built lots and putting them on the gallery with the tag “#timelineadventure” as I work through the challenge myself. My sims Origin tag is IllusoryThrall, feel free to toss me a follow. I will link each generation’s pre-built lots in boxes like this on this page for each generation – so if you’re not a builder, you can still easily play this challenge. I will eventually get to building lots for all generations, but for now it’s just the first few generations that I have completed. All lots mentioned on these pages are CC-free and playable! Also, if you build a lot that qualifies as those two things and want it included in these lists, please just drop me a comment here or a message at IllusoryThrall on the sims forums, I will check it out and add it if it fits!

Gen 31: Getting an Education (1995s)

After a miserable childhood, you vowed to never let another child be forgotten and left behind. For this reason, you aim to be a teacher, and to have a large, close-knit, and happy family. You get out of your childhood home as soon as you possibly can, and move into the dorms at University, determined to be a huge part of campus activities. You find lots of friends, and a lot of fun, but you never forget your original aspiration and your studies. After graduation, you jump into your chosen career with gusto, and immediately marry and start a family. Your children will never want for anything, and they will always be the best at whatever they choose to be.

Town: Britechester (Gibbs Hill)

Lot Traits: Study Spot, Good Schools, Child’s Play

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Genius, Overachiever, Family Oriented

Aspiration: Academic

Career: Education (Professor)

Gen 31 Goals:

• Complete the Academic Aspiration on main sim.
• Complete the Education career in the professor branch.
• Skills to be maxed: Research & Debate and Parenting. (on main sim)
• Marry someone you meet at college. The wedding should take place right after graduation.
• Have at least three children, and have high relationships with each. Push them to be over-achievers, and have each child join in after-school activities.
• Each child must get at LEAST three positive Parenthood traits upon aging into Young Adulthood, and have an “A” in school.
• Your heir’s traits will be: Self-Absorbed, Creative, and Party Animal; and their aspiration is Party Animal.

Generation 31 Lots:

Gen 32: Setting the Trends (2000s)

Your parents always wanted the best for you, and an almost too-perfect childhood only made you crave the spotlight even more. As a child, you are drawn to fashion, and the glitz and glamour of the runway. Once you’re all grown up and can shed the burden of a family that always seemed to expect too much of you, you immediately start setting the trends. Seeing your designs in the bright lights is your dream come true. You find celebrity love and begin to dress up your kids in the type of clothes you wish you had always had.

Town: San Myshuno (Fashion District)

Lot Traits: Party Place, Home Studio, Natural Light

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Self-Absorbed, Creative, Party Animal

Aspiration: Party Animal

Career: Stylist (Trendsetter)

Gen 32 Goals:

• Complete Party Animal Aspiration on main sim.
• Complete Stylist Career in the Trendsetter branch on main sim.
• Skills to be maxed: Writing, Charisma, Painting, Photography, DJ Mixing. (all on main sim)
• Meet, woo, and marry a celebrity.
• Must have at least one child.
• Make sure to give everyone in the household makeovers every time they age up, and each household member should have at least two outfits for each outfit category.
• Your heir’s traits will be: Genius, Geek, Loner; and their aspiration is Computer Whiz.

Generation 32 Lots:

Gen 33: Hack the Planet (2005s)

Being in the limelight was never your thing. You grew up with your parents being obsessed with it, and you quickly soured to it. You spend all your time in your room on your computer, finding ways to get into trouble. Once grown up, your experience in computers netted you some great opportunities to start your own business, and you took them and ran with it. Finding love, however, wasn’t as easy. You struggle to find a mate, and have two failed fiancés before you finally find one that sticks with you.

Town: Oasis Springs (Parched Prospect)

Lot Traits: Fast Internet, Penny Pixies, Gnomes

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Genius, Geek, Loner

Aspiration: Computer Whiz

Career: Tech Guru (Start-up Entrepreneur)

Gen 33 Goals:

• Complete Computer Whiz Aspiration on main sim.
• Complete Tech Guru career in the Start-up Entrepreneur branch on main sim.
• Skills to be maxed: Programming, Logic, Video Gaming. (on main sim)
• Meet and woo at least two separate partners who get engaged to you, but later break it off before you find “the one” that stays with you.
• Have at least one child.
• Your heir’s traits will be: Adventurous, Proper, Active; and their aspiration is Extreme Sports Enthusiast.

Generation 33 Lots:

Gen 34: Adrenaline Junkie (2010s)

You grew up surrounded by technology in a fast-paced world. This became a way of life for you, and you embrace the adrenaline rush that the speed of life gives you. When you hear about Mt. Komorebi, you know you’ve found your new home. You find a job just to pay the bills, but immediately regret the long hours forced on you by Corporate America. Somehow you find ways to slack on the job and still get promotions, and you take as much time off as you possibly can – spending all your free time on the slopes of the mountain. You marry someone who is a part of your climbing group, and after watching the fun that other parents are having with their children in the white wonderland, you and your mate resolve to fill your home with happy voices.

Town: Mt. Komorebi (Yukimatsu)

Lot Traits: Fast Internet, Bracing Breezes, Teen Neighborhood

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Adventurous, Proper, Active

Aspiration: Extreme Sports Enthusiast

Career: Salaryperson (either branch)

Gen 34 Goals:

• Complete the Extreme Sports Enthusiast aspiration on main sim.
• Complete the Salaryperson career in either branch.
• Purchase the Professional Slacker, Entrepreneurial, and Mentor Reward Traits on main sim.
• Keep your vacation days at 0 – in other words, when you get one, use it.
• Master the Rock Climbing, Fitness, and either Snowboarding or Skiing (or both if you’re an over achiever!).
• Marry someone you meet on the mountain and have at least 4 children.
• Teach your children to ski or snowboard (each child can pick what they like best) by mentoring them on the slopes. All must have at least level 6 in one or the other before they turn into a Young Adult.
• Same sex-marriage is now legal.
• Your heir’s traits will be: Self-Absorbed, Outgoing, Squeamish; and their aspiration is Super Parent.

Generation 34 Lots:

Gen 35: The Age of the Cyber Web (2015s)

You grew up connected to the slopes of Mount Komorebi, immersed in the white world it offered your family. However, nature isn’t your idea of a good time. All the creepy critters out there can keep their pristine white world, for all you care. The perfection of your seemingly idyllic family becomes ingrained, and your easy access to the rest of the world through the web causes you to fall head over feet into the trap of technology. You love being connected and having everything at the tips of your fingers. You love social media and making videos for viewers. Your obsession with perfection turns into a need to have the perfect family and perfect life, even in it means being dishonest to portray it to the world. Now that you are an influencer, you have the world watching your every move, and you do whatever it takes to make sure that they only see your “good side”.

Town: Brindleton Bay (Whiskerman’s Wharf)

Lot Traits: Fast internet, Sunny Aspect, Child’s play

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Self-absorbed, Outgoing, Squeamish

Aspiration: Super Parent

Career: Social Media (Internet Personality)

Gen 35 Goals:

• Complete Super Parent Aspiration on main sim.
• Complete the Social Media Career in the Internet Personality branch on main sim.
• Skills to be maxed: Charisma, Media Production, Parenting. (on main sim)
• Become a famous influencer with a large following.
• Post your every move on social media.
• Have the “perfect” family…. at least on camera.
• Grow to hate your spouse but never divorce.
• Have at least two children.
• Your heir’s traits will be: Materialistic, Good, Dancing Machine; and their aspiration is Mansion Baron.

Generation 35 Lots:

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Updated: 1/16/25

Once you’re ready to play, grab a copy of my Timeline Adventure Challenge Tracking Spreadsheet to track your progress!

Note on Lots: I will be building pre-built lots and putting them on the gallery with the tag “#timelineadventure” as I work through the challenge myself. My sims Origin tag is IllusoryThrall, feel free to toss me a follow. I will link each generation’s pre-built lots in boxes like this on this page for each generation – so if you’re not a builder, you can still easily play this challenge. I will eventually get to building lots for all generations, but for now it’s just the first few generations that I have completed. All lots mentioned on these pages are CC-free and playable! Also, if you build a lot that qualifies as those two things and want it included in these lists, please just drop me a comment here or a message at IllusoryThrall on the sims forums, I will check it out and add it if it fits!

Gen 26: Protest, Activism, & War (1970s)

You grew up around animals, ignored by the parent that should have loved you, and instead only loved anything with fur. Your parent felt their life goal was to save every single pet in the entire universe, which seemed a silly sort of goal. Rather, you decide you want to help a more worthy cause – the environment. You can see how the planet has become industrialized and dirty. All you want in life is to save the planet before things get any worse. The Vietnam War only solidifies your ambition. You believe that everything should be natural and that you must pull away from the processed world entirely. You leave your hometown and move closer to the volcano and the only “wild” area left in the Sulani Islands. You feel deeply, spiritually, connected to the Islands, and you swear you can feel the presence of the ancestors all around you, approving of your crusade.

Town: Sulani (Lani St. Taz)

Lot traits: Great Acoustics or Oceanic Paradise, Island Spirits, Sunny Aspect

Lot Challenges: Off The Grid

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: High Maintenance, Vegetarian, Snob

Aspirations: Inner Peace (and/or) Self-Care Specialist (and/or) Zen Guru

Career: Conservationist

Gen 26 Goals:

• Complete Career on main sim.
• Complete at least one of the listed Aspirations on main sim.
• Max the Guitar, Fitness, and Photography skills (on main sim)
• “Save Sulani” by keeping it clean and the trash picked up. (The islands must be pristine by the time the heir moves out.)
• Marry a mermaid. (Or have the sim you marry become one through the use of Mermadic Kelp – which can be bought on the Rewards store for 500 points.)
• Have at least three children.
• Your heir’s traits will be: Art Lover, Horse Lover, and Foodie; and their aspiration will be Expert Nectar Maker.
• Starting in the 1970s, Tiny Homes started to become a thing. Use at your discretion.

Generation 26 Lots:

Community Lots Unlocked after this generation: Arts Center, Karaoke Bar

Gen 27: Nectar Valley (1975s)

You were brought up to love nature, and your parents expected you to follow in their footsteps as an activist for nature, but you felt your destiny lay elsewhere. A burgeoning nectar industry was growing in Napa Valley, California, and you couldn’t think of anything more idyllic than running a Nectary of your own, so you packed your bags and moved back to the mainland. Starting a nectary was hard work, but soon your love of parties and friends started bringing people from far away to try your nectars. Slowly, you began turning a profit – enough to afford a luxury you’d always craved… horses. You build a fancy barn and buy a fancy horse, and start competing in the local jumping circuit. Eventually, you even start a family, but inexplicably, your heir seems to see monsters in every shadow, despite the luxury they have grown up in, and you quickly grow apart.

Town: Chestnut Ridge (Rider’s Glen)

Lot Traits: Great Soil, Homey, Party Place

Lot Challenges: Wild Prairie Grass

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Art Lover, Horse Lover, Foodie

Aspiration: Expert Nectar Maker

Career: Running your own nectary and farm, selling nectar for profit

Gen 27 Goals:

• Your first job is to become human again (if you were born mermaid, which is likely). Take two Mermadic Kelp, and walk into the ocean.
• Main sim must max the following skills: Gourmet Cooking, Nectar Making, Charisma, Mixology, and Horse Riding.
• Grow all the crops for your nectar on your own farm, and have a cellar to age your nectars.
• At least once a week, throw a party (of any type) with your friends, and be sure to always serve some of your own nectar.
• Your main sim must have at least 10 good friends that are NOT a part of your household or family.
• Your main sim’s partner must get along with your family and be “respectable” (no evil or mean traits – interpret this as you will).
• Your wedding must be held on your Nectary property.
• When you can afford it, (and after you have had your first child), build a fancy barn, buy a “fancy” (not rescued or adopted) horse, and begin competing in local jumping competitions. (if you want, you can go back and finally get your main sim to complete the Championship Rider Aspiration).
• By the end of the generation, you must have at LEAST 25 sim-created paintings of Excellent quality or better, whether painted by someone in your family, your main sim, or bought elsewhere. (ex. plopsy, romance fest, arts district in Myshuno, sometimes can buy paintings in Sulani as well)
• Must have at least 2 children.
• Your heir’s traits will be: Paranoid, Socially Awkward, and Hates Children; and their aspiration will be Chief of Mischief.

Generation 27 Lots:

Community Lots Unlocked after this generation: Spa

Gen 28: Cold War Paranoia (1980s)

You were brought up to love nature, and your parents expected you to follow in their footsteps and take care of the family nectary, but you felt danger around every corner. Ferreting out the truth of the matter began to consume your every day, and before you, you knew your true calling was as a spy. You left home and your idyllic life at the nectary for spy academy and never once looked back. This was the time your country needed you, and yes, everyone WAS out to get you!

Town: San Myshuno (Arts Quarter)

Lot Traits: Private Dwelling, Gnomes, Mean Vibe

Lot Challenges: Cursed

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Paranoid, Socially Awkward, Hates Children

Aspiration: Chief of Mischief

Career: Secret Agent (Villain)

Gen 28 Goals:

• Complete Chief of Mischief aspiration on main sim.
• Complete Secret Agent Career in the Villian branch (it goes to level 11!)
• You must move to a different apartment in a different district in the city at least three times this generation, starting in the Arts District. The timing on this is completely up to you. I also leave which district you move to up to you in the middle, but aim to be living in Uptown at the end of the generation.
• Master the Fitness and Mischief skills on your main sim.
• Marry and have at least 1 child.
• Your main sim must spend very little time with their child(ren), and barely get to know them.
• Your child(ren) can have no more than three child-age friends each, and have to find new ones every time the family moves (becoming enemies with the old ones).
• Your heir’s traits will be: Creative, Perfectionist, Outgoing, and their aspiration will be Mt. Komorebi Sightseer.

Generation 28 Lots:

Community Lots Unlocked after this generation: You may now visit the Onsen in Mt. Komorebi

Gen 29: Bringing Modern In (1985s)

You barely knew your parents, and their constant suspicion and paranoia really grated on your nerves. All you really wanted was to settle down in one place, raise a happy family.. and perhaps be the change you wanted to see in the world. You believed times were a-changing, and you wanted to help others make positive changes in their homes and lives, too.

Town: Mt. Komorebi (Wakaba)

Lot Traits: Home Studio, Natural Light, Peace and Quiet

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Creative, Perfectionist, Outgoing

Aspiration: Mt. Komorebi Sightseer

Career: Interior Decorating

Gen 29 Goals:

• Complete Mt. Komorebi Sightseer Aspiration on main sim.
• Max career on main sim.
• Skills to be maxed: Painting, Photography, Charisma (on main sim)
• Do your best to make-over houses in the world, bringing the modern generation to the houses.
• Have at least 2 kids.
• Starting this generation, Computer Club afterschool activity is allowed.
• Your heir’s traits will be: Child of the Village, Nosy, and Cringe; their aspiration will be either Discerning Dweller or Fount of Tomarani Knowledge.

Generation 29 Lots:

Gen 30: Nosing Around the Neighborhood (1990s)

Your parents believed in light and goodness and that everyone really just needed a cozy place of their own to live in to be happy. You, on the other hand, knew better. Everyone had secrets and the juicier the secret, the more you wanted to know it. You found out quickly that you had a talent for weaseling your way in and finding out all the dirty little secrets people probably should keep hidden… and you make a living from it. Rising quickly among the ranks of journalism, you spend your life hunting down every secret that isn’t completely nailed down. (And if it’s nailed down, you’re only more determined to ferret it out!)

Town: Tomarang (Koh Sahpa)

Lot Traits: Convivial, Mean Vibe, Singles Hangout

Lot Challenges: Maintenance Troubles

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Child of the Village, Nosy, Cringe

Aspirations: Discerning Dweller/ Fount of Tomarani Knowledge

Career: Writer (Journalism Branch)/ Tenant

Gen 30 Goals:

• Complete Discerning Dweller Aspiration on main sim
• Complete Fount of Tomarani Knowledge on main sim
• Reach Level 10 of the Writer career in the Journalism Branch on main sim.
• Master Writing (main sim)
• Master Charisma (main sim)
• Master Mischief (main sim)
• Have at least one child, and ignore it (The child must be reared by spouse or nannies)
• Spend all your main sim’s time digging in garbage, finding out secrets, and even breaking into houses to spy on people. Feel free to use the StrangerVille bugs, and you can install a burglary mod if you’d like.
• Your heir’s traits will be Genius, Overachiever, and Family Oriented; their aspiration will be Academic.

Generation 30 Lots:

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Updated: 1/16/25

Once you’re ready to play, grab a copy of my Timeline Adventure Challenge Tracking Spreadsheet to track your progress!

Note on Lots: I will be building pre-built lots and putting them on the gallery with the tag “#timelineadventure” as I work through the challenge myself. My sims Origin tag is IllusoryThrall, feel free to toss me a follow. I will link each generation’s pre-built lots in boxes like this on this page for each generation – so if you’re not a builder, you can still easily play this challenge. I will eventually get to building lots for all generations, but for now it’s just the first few generations that I have completed. All lots mentioned on these pages are CC-free and playable! Also, if you build a lot that qualifies as those two things and want it included in these lists, please just drop me a comment here or a message at IllusoryThrall on the sims forums, I will check it out and add it if it fits!

Gen 21: Chaos Versus Order (1939-1945)

The Depression finally ended, but things didn’t get better – instead, the world up and went to war again. You’d heard stories all your life about the antics of your great-great-grandfather in the first world war – but you wanted something different. You wanted to become a great leader. So you went into the Military as was expected, but you aimed to be an Officer so you could send more money home to your family. This also gave you a sense of prestige and power that you desperately needed after growing up in such a horrible state. Your family lives in base housing and you visit when you can.

Town: Copperdale (Plumbite Cove)

Lot Traits: Homey, On the Ley Line, Child’s Play

Lot Challenges: Gremlins

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Active, Self-Assured, Neat

Aspiration: Bodybuilder

Career: Miltary (Officer)

Gen 21 Goals:

• Complete the Bodybuilder Aspiration on main sim (provided you live through the war).
• Max Fitness and Charisma (on main sim – or as close to max as you can get before a bad roll)
• Try to max your career – however, don’t stress too much if you can’t since leaving for the war will make this extremely difficult.
• To simulate the war, your main sim will again be moving out for periods of time while they are deployed. Nearly 40% of the US population were listed as casualties because of the war, so your chances of your main sim dying are much higher. Just like we did in WW1, have your main sim get their job, get married, and get the wife pregnant before the first deployment. Each deployment (for ease of play) works nearly the same way: this time, move your main sim out of the main household for 6 days, then back in for one, getting the wife pregnant again while home and rolling to see what happened to your main sim during their deployment (see below for roll information). Then, repeat the process. EACH time your sim is deployed, you re-roll to see what happens. For WW1, we had a total of three deployments, but for WW2, the war was longer, so there are more deployments. There are five deployments this time, with the last one being only 3 days like last time (this makes the total time the war is going 31 days.) Yes, this means you have to roll five separate times. For the roll: roll a ten sided die – a 1 or 2 means your sim died outright (move them back in and kill them however you wish); a 3 or 4 means they were wounded and are immune from any further deployments. Rolling 5 – 10 (a 0 on the die) means your sim is (at least physically) healthy and continues the pattern. Once the war is over, you have time to work on your main sim’s skills and career (provided they lived).
• Provide a safe and secure home for your children. All disobediences must be punished strictly.
• Have at least 4 children. (or as many of them as you can before your sims dies, if you happen to roll badly).
• Your heir’s traits will be: Self-Absorbed, Neat, Creative; and their aspiration will be Master Actor/Actress.

Generation 21 Lots:

Gen 22: Hollywood’s Golden Era (1950s)

You grew up on a military base in a strict household. You were expected to find a good career and make something of yourself. However, you wanted to act. You wanted your whole world to revolve around the Silver Screen. You move to the expensive side of Del Sol Valley and become an actor or actress. You rise in popularity and soon become one of the most sought after actors (or actress) of the decade.

Town: Del Sol Valley (The Pinnacles)

Lot traits: Penny Pixies, Good Schools, Celebrity Home (this last one is only unlocked once sim becomes famous – add this lot trait once your sim gets their third celebrity star)

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Self-Absorbed, Neat, Creative

Aspiration: Master Actress/Actor

Career: Actor/Actress

Gen 22 Goals:

• Complete Master Actress/Actor Aspiration on main sim.
• Complete Actor/Actress career on main sim.
• Skills to be maxed: Acting, Comedy, Mixology and Singing (on main sim)
• Become a famous actor. By the time your heir moves on, have your main sim get all five stars as a celebrity.
• Marry five times. Divorced three times, widowed once (kill off this sim however you wish). One spouse outlives you and ends up taking care of the kid.
• Have one child, and ONLY one child, unless you “luck out” and get twins or triplets. You may choose which of the three surviving spouses the heir will come from as you wish. (Do not pick from the one that dies, or the one you stay married to until your death).
• Your heir’s traits will be: Loner, Romantically Reserved, and Socially Awkward; their aspiration will be Five-Star Property Owner.

Generation 22 Lots:

Gen 23: Seeking Obscurity (1955s)

After being stuck with a Celeb for a parent, you had no desire to EVER be in the limelight again… but you knew that you’d have to support yourself somehow. So, you took your inheritance and ran with it. You bought a lovely big home, and subdivided it into apartments with the intention of being the best landlord there ever was. The problem? You’ve never been the best at social situations. So you dive into your ability at handiness, and vow to at least make sure that everything in your tenant’s units is at least working right all the time, even if your love life isn’t…

Town: Ciudad Enamorada (Plaza Mariposa)

Lot traits: Private Dwelling, Peace & Quiet, Homey

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Loner, Romantically Reserved, Socially Awkward

Aspiration: Five-Star Property Owner

Career: Landlord

Gen 23 Goals:

• Complete the Five-Star Property Owner aspiration on main sim.
• Master Charisma (main sim)
• Master Handiness (main sim)
• Find someone and get married (do not have to STAY MARRIED).
• Have children until you have 1 boy to be heir – the heir does not have to be born to your first marriage, nor even in wedlock.
• Spend as much time with your heir as possible, and become the very best of friends with them.
• The heir must maintain a “best friend” relationship with their main sim parent, even after this sim is divorced and is living out of the main household.
• When your heir moves out, the main sim WILL move out with them, and live the remainder of their life with the next generation.
• Your MALE heir’s traits will be Active, Bro, Ambitious; and their aspiration will be Serial Romantic.

Generation 23 Lots:

Gen 24: Wrapped up in Sports (1960s)

Your parents never seemed to get along, but at least one of your parents was ALWAYS there for you. They were almost always home (if they weren’t fixing the neighbor’s water heater) and they came to every sporting event you were in, cheering you on. Before long, with their support, you began to have dreams of greatness, and vowed to pursue a career in Athletics. Even after moving out on your own, this parent and you stay in touch and they inspire you to be one of the “greats”.

Town: Copperdale (Prescott Square)

Lot traits: Bracing Breezes, Sunny Aspect, Good Schools

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Active, Bro, Ambitious

Aspiration: Serial Romantic

Career: Athlete (Pro Sports)

Gen 24 Goals:

• One way to play this generation would be sending your sim to University, and have them join the sports team there, then get into the Athletic career and “start” the generation only after they’ve graduated, but I leave this choice up to you.
• If you do decide University is for you – have your sim live at their parent’s home while they study, and commute to classes and sports games. Once graduated, then move to the new home area, pick out the correct Lot Traits, and truly begin the generation.
• If you skip University – start the generation as you do normally: move to your new home, set Lot Traits, get your career, etc.
• Complete the Serial Romantic Aspiration on Main sim.
• Complete Career on main sim.
• Skills to be maxed: Fitness, Charisma (on main sim)
• Never marry, but have LOTS of girlfriends or boyfriends (or both?). Continue to have children as a result of one night stands until you have a girl and dote on that girl, mostly ignoring any other children.
• Your heir must be female and have the traits: Cheerful, Unflirty, and Cat or Dog Lover (your choice); while aspiration will be Friend of the Animals.

Generation 24 Lots:

Gen 25: Raising the Hackles (1965s)

You grew up in a supportive single-parent environment, with pets that you adored. Because of this, you couldn’t help but focus on animals. You love them all and want to save them all. Your entire focus is on the animals, leaving your social skills with people floundering in the dust. You try to make friends and find love, but your idea of finding companionship always requires you to be at the bottom of a bottle to get up the courage. You have a child but it is a result of a drunken one-night stand that you wish you could forget. Hence, you hire help, and go back to helping the animals instead.

Town: Brindleton Bay (Sable Square)

Lot traits: Breeding Grounds, Training Ground, Pet (you choose cat or dog) Hangout

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Cheerful, Unflirty, Cat/Dog Lover (your choice)

Aspiration: Friend of the Animals

Career: Own a Vet Clinic

Gen 25 Goals:

• Complete Friend of the Animals aspiration on main sim.
• Skills to be maxed: Pet Training, Logic, and Veterinarian (all on main sim)
• Own and run a highly rated vet clinic.
• Have at least three pets at all times.
• Never marry – you are too busy with your vet clinic and your pets for romance. Your main sim’s attempt at romance is a series of one-night stands. Never have a girlfriend or boyfriend, either. The romance always falls apart before your sim gets that far.
• Have a child by one of these one night stands – this will be your only child (unless, of course, it’s multiples). If your main sim is a male, you can have the mother move in until after the baby is born. As soon as the baby is born, the mother must again move out.
• Your child is mostly ignored by you, and is raised mostly by nannies and babysitters.
• Your heir must be FEMALE, and their traits will be: High Maintenance, Vegetarian, and Snob; their aspiration will be one of three: Inner Peace, Self Care Specialist, or Zen Guru (your choice).

Generation 25 Lots:

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Updated: 1/16/2025

Once you’re ready to play, grab a copy of my Timeline Adventure Challenge Tracking Spreadsheet to track your progress!

Note on Lots: I will be building pre-built lots and putting them on the gallery with the tag “#timelineadventure” as I work through the challenge myself. My sims Origin tag is IllusoryThrall, feel free to toss me a follow. I will link each generation’s pre-built lots in boxes like this on this page for each generation – so if you’re not a builder, you can still easily play this challenge. I will eventually get to building lots for all generations, but for now it’s just the first few generations that I have completed. All lots mentioned on these pages are CC-free and playable! Also, if you build a lot that qualifies as those two things and want it included in these lists, please just drop me a comment here or a message at IllusoryThrall on the sims forums, I will check it out and add it if it fits!

Gen 16: Country Living (Victorian Continued – 1890 AD – 1900 AD)

Your parents were obsessed by the supernatural, and their travels to different haunted houses all the time sparked an intense desire in you to be home with your family. Your parent moves with you when you move out, convinced that the best thing they could do is be there while you start your family. The bucolic farm life calls to you, and you throw yourself into raising animals, caring for your land, and spending time with your growing family.

Town: Henford-On-Bagley (Old New Henford)

Lot traits: Great Soil, Peaceful and Quiet, Homey

Lot Challenges: Off The Grid, Wild Foxes, Simple Living

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Christmas – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Animal Enthusiast, Loves Outdoors, Family Oriented

Aspiration: Country Caretaker

Career: Self-Employed Farmer

Gen 16 Goals:

• Your last generation’s Main Sim will be living with you. Make sure you provide them a small apartment, and keep a close relationship with them.
• Complete the Country Caretaker Aspiration on your main sim.
• Max the Gardening, Fishing, and Cooking skills on your main sim.
• Max Knitting, and Cross-Stitching skills. (does not have to be on main sim)
• Have at least 3 children.
• Own at least one cow, two Llamas, 6 chickens, and maintain a large selection of plants in your garden.
• Build a Pond somewhere on your property and stock it with various types of fish.
• Build a Family graveyard to bury your parent (when they die).
• Your heir’s traits will be: Active, Goofball, and Loves the Outdoors, and their aspiration will be a choice between Jungle Explorer and Archaeology Scholar.

Generation 16 Lots:

Gen 17: Into the Tombs (Edwardian 1901 AD – 1910 AD)

Your parents doted on you and their farm. They instill in you a desire to travel the world and study what came before. Hiring a caretaker to care for your home, you begin travelling to distant lands and learning about ancient cultures. You uncover old artifacts and learn a new language. You fall in love with someone from far away but they die long before their time is up and leave you to raise your child with only the help of your caretaker.

Town: Willow Creek (Courtyard Lane)

Lot traits: Sunny Aspect, Homey, Bracing Breezes

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Christmas – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Active, Goofball, Loves the Outdoors

Aspiration: Archaeology Scholar and/or Jungle Explorer

Career: Self-Employed Archaeologist

Gen 17 Goals:

• Complete One (or both) of the listed Aspirations on your Main Sim.
• Max the Archaeology, Fitness, and Selvadorian Culture skills on your main sim.
• Move in a townie or created sim of your choice to leave at home to care for home and family.
• By this generation, Electricity was starting to become more common. It’s still rare, but your family can afford to have your home hooked up – in other words, no more Off The Grid Lot Challenge!
• Must marry a native of Selvadorada.
• Have children until you have a boy – this will be your heir. (Yes, you can use carrots to “force” a boy on your first child if you want.)
• Spouse must die shortly after the boy child is born, preferably during his toddlerhood. After this, have your main sim become distant with all the children.
• Explore the entire jungle in Selvadorada.
• Your heir must be male and their traits will be: Active, Good, and Self-Assured, and his aspiration will be Big Happy Family.

Generation 17 Lots:

Gen 18: The War to End All Wars (WWI – 1914 AD – 1918 AD)

When you were a teenager, the world up and went to war. One of your parents died young and the other never properly mourned their loss. You had a few friends but no one to really lean on. You felt abandoned and the discipline and brotherhood of the military seemed to call to you. You loved your country and wanted fight for the cause, enlisting as soon as you were able gladly. As for love, you fell in love shortly before heading off to war and the two of you married quickly, conceiving your first child before shipping out. When you arrive home from the war, you have some personal demons to fight through, but your big family from the times you were home on leave is there to help you through. However, jobs are scarce and supporting all those children is expensive, causing you to emigrate to the New World in search of better times ahead.

Town: Newcrest (Bridgeview)/San Myshuno

Lot Traits: Homey, Good schools, On the Ley Line

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Christmas – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Active, Good, Self-Assured

Aspiration: Big Happy Family (does not need to be completed during this generation)

Career: Military (Covert Operator) – do NOT need to Max this career, you will not have time.

Gen 18 Goals:

• Max the Fitness and Handiness skills on your main sim (provided he isn’t killed or wounded, obviously.) Your spouse must Max the Parenting skill.
• Go off to war for long periods of time – Move your main sim out of the house for 7 days, then, move them back into the household for 1 day to simulate “leave” (making sure to get the spouse pregnant again while home). Do this once again, to total 16 days, then move out for the final deployment of 3 days for a grand total of 19 days. For EACH deployment, roll a 10 sided die. If you roll a 1, your main sim didn’t survive the deployment – move him back in and have him die of whatever method works the best for you. If you roll a 2, he was injured during the deployment and moves back home permanently, skipping any future deployment. If your sim was injured, change his “Self-Assured” trait to “Gloomy” using either a re-traiting potion or the cas.fulleditmode cheat, and he will remain home during the rest of the war. Rolling any other number means your sims is just fine, and can continue with deployments until the end of the war.
• When the war is over (19 days after the first deployment starts) – have your main sim quit his military job (if he survived, obviously), and move the entire household to The Old Salt House lot in San Myshuno (Spice District) and build them a house. This simulates the entire family moving to the United States.
• Have at least 5 children (unless your main sim dies, obviously). If you haven’t had five yet by the time the war ends, keep trying.
• After the war, have your main sim become distant with his family, especially if he got wounded during the war.
• Your heir’s traits will be Evil, Mean, and Hot-Headed, and their aspiration will be Public Enemy.

Generation 18 Lots:

Community Lots Unlocked after this generation: National Park, Nightclub

Gen 19: Gangsters and Flappers (1920s)

You grew up in a time of war in a huge family. Sometimes food and other necessities were hard to come by. Things didn’t get a whole lot better after your family emigrated to the United States following the war. You turned to the streets in order to survive, falling into the wrong crowd and starting a life in the underground world. You obeyed no rules but your own, and eventually became the most fearsome mobster in the city.

Town: San Myshuno (Spice District)

Lot traits: Penny Pixies, Convivial, Party Place

Lot Challenges: None

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Evil, Mean, Hot-Headed

Aspiration: Public Enemy

Career: Criminal (Boss Branch)

Gen 19 Goals:

• Complete Public Enemy Aspiration on main sim.
• Complete Career on main sim.
• Max the Logic, Mischief, Fitness, and Charisma skills on your main sim.
• Become a mob boss. Use the club feature to create your own “mob”.
• Must throw parties to flaunt your power and money – at least one per week.
• Marry the child of an enemy.
• Your spouse hates you but will never leave you because they are terrified of you.
• Have at least 2 children.
• Starting this generation, you are allowed to follow your sims to High School – although you may want to give the High School and auditorium lots a makeover first.
• Also starting this generation: you may join all after school activities EXCEPT Computer club! (for obvious reasons)
• Your heir’s traits will be: Noncommittal, Family Oriented, Gloomy, and their aspiration will be Renaissance Sim.

Generation 19 Lots:

Gen 20: The Great Depression (1929 – Late 1930s)

Your parent was a notorious gangster, so you had never wanted for money or material goods. You move away, but, even then, money isn’t an issue, because your parents provide you with a generous inheritance. This all changes when the stock market crashes. Not only do you and your family lose everything, but you can also no longer keep a job for any length of time, and supporting your new family becomes next to impossible. Every Simoleon earned is a struggle. You are kicked out of your home, and the only place you can find to live is a horrible slum. Despite hating it, you know you must survive. Sticking together and hard work is the only way to do this so that your family can live on.

Town: Del Sol Valley (Mirage Park)

Lot Traits: None!

Lot Challenges: Grody, Filthy, Cursed, Off The Grid

Holidays:

• Spring: Easter – Give Flowers, Egg Hunt, Grand Meal, Flower Bunny
• Summer: Fourth of July – Barbeque, Fireworks, Drinking, Party Spirit
• Fall: Halloween – Remembrance, Spooky Spirit, Trick or Treat, Mischief Spirit
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Non-committal, Family Oriented, Gloomy

Aspiration: Renaissance Sim

Career: Whenever you hit level 4 of a career, you must quit your job and find a new one (Exception: the first career you choose, you will go to level 5). You can never get promoted past this point. If you run out of options for a career from the following list, you can no longer get a job. Odd jobs are also allowed (although, you may want to restrict which ones you can do to the ones that don’t require modern technology). (Allowed careers: Athlete, Business, Criminal, Culinary, Entertainer, Painter, Writer, Gardener, Education, and all part-time Careers. I suggest NOT having your sim “work from home” in any career that allows this because that usually involves technology.)

Gen 20 Goals:

• Start this generation as usual, by moving out to a lot in the new area and building a home (do not start out with any lot traits!). Find a job in any of the above listed careers, then find a spouse and start your family. Do not add lot challenges yet!
• As soon as you are promoted to Level 5, the stock exchange crash happens. Immediately quit your job (this job is then crossed off the list of available jobs), bulldoze the house, set your money at 5000 Simoleons with a money cheat, and add in your new lot traits (listed above). All the riches your family had previously made are now gone and this is all the money you have to build your new home. (Do not expect a rescue from your parents, either – they lose everything in the crash, as well.) Your family will never recover the rest of the riches you had saved over the generations – you are starting completely over in the money department.
• Also: Yes, you read that right, once the stock market crashes, you are back to having no electricity again. I hated doing this to you guys, but keeping the lights on just wasn’t realistic. Add all listed Lot Challenges to your lot.
• One other thing: Prohibition was a thing in this time, so do NOT build or visit any commercial lots with a bar (unless designed like a speakeasy) and there are no bars allowed on your home lot.
• Your Main Goal: Survive this generation!
• Complete the Renaissance Sim Aspiration on your main sim.
• Your aspiration requires you to choose 6 skills to get to level 8. Take three of those to Max. For this generation only, you are free to pick what those skills are (barring the Mixology skill, of course)!
• Have at least 3 children (one must be a male to be heir)
• Your heir must be male and their traits are: Active, Self-Assured, Neat, their aspiration is Bodybuilder.

Generation 20 Lots:

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Updated: 1/16/25

Once you’re ready to play, grab a copy of my Timeline Adventure Challenge Tracking Spreadsheet to track your progress!

Note on Lots: I will be building pre-built lots and putting them on the gallery with the tag “#timelineadventure” as I work through the challenge myself. My sims Origin tag is IllusoryThrall, feel free to toss me a follow. I will link each generation’s pre-built lots in boxes like this on this page for each generation – so if you’re not a builder, you can still easily play this challenge. I will eventually get to building lots for all generations, but for now it’s just the first few generations that I have completed. All lots mentioned on these pages are CC-free and playable! Also, if you build a lot that qualifies as those two things and want it included in these lists, please just drop me a comment here or a message at IllusoryThrall on the sims forums, I will check it out and add it if it fits!

Gen 11: Georgian Era Power (1714 AD – 1830 AD)

Powdered wigs and full skirts are in fashion. Social stations have officially divided the classes, but you were fortunately born into a wealthy family. You have left behind the islands (and your fins), and returned to society. The king has awarded your family with pardon for the crime of Piracy, and a noble title for your work in fighting the witches and werewolves. You love a party and the social scene. You want nothing more than to be popular and well respected by your peers. You’ve become greedy and obsessed with your social status. You become a politician to advance this and keep the lower classes at bay. You have children only because it is expected of you but you have no desire to interact with them until they are older.

Town: Newcrest (Llama Lagoon)

Lot traits: Convivial, Party Place, Mean Vibe

Lot Challenges: Off the Grid

Holidays:

• Spring: St. Valentines Day – Give Flowers, Go on a Date, Romantic Spirit
• Summer: None. Just filled with parties.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Christmas – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit, Attend Holiday Ceremony

Traits: Perfectionist, Hates-Children, Noncommittal

Aspiration: Friend of the World

Career: Politician (politician branch)

Gen 11 Goals:

• You love a good party. You must throw a party every weekend, as well as for any birthdays (except babies), weddings and during holidays.
• You may use NPC’s like maids and butlers as servants. Optionally, moving in a townie sim to be your servant is also okay so long as they have their own area of the home.
• Max the Charisma and Logic skills and one musical instrument of your choice on your main sim.
• Marry but have several (at least two) extra-marital affairs.
• Have at least two children by your wife (and however many you want out of wedlock – only the ones by your wife are eligible to be heir, though.)
• Have nothing to do with your children until they are teenagers on your main sim – unless it is to do mean interactions. (Interactions once they are teenagers are at your discretion – feel free to tell the story however you wish.)
• Starting in this generation, you can now “Woohoo” instead of always “Try for Baby”!!
• Your heir’s traits will be: Good, Romantic, Bookworm, and their aspiration will be Bestselling Author.

Generation 11 Lots:

Community Lots Unlocked after this generation: Vet Clinic; Library (the first ones were founded in the mid 1700’s)

Gen 12: Regency Era Lover (1795 AD – 1837 AD)

Your father was a greedy man and it was hard to admire him. You always had more of a romantic and kind side. You moved away from the family home and bought a small estate near the seashore. You love to read and write. You always had a wild imagination and dreamed of becoming a writer. So, now you write books under a pen name so that no one knows who you really are. You are the child of a lord, after all.

Town: Brindleton Bay (Cavalier Cove) (If you have the Tartosa world, use the Terra Amorosa district as your home district. Cavalier Cove and and Porto Luminoso will both be commercial in this case.)

Lot Traits: Home Studio, Peace and Quiet, Penny Pixies

Lot Challenges: Off the Grid

Holidays:

• Spring: St. Valentines Day – Give Flowers, Go on a Date, Romantic Spirit
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Winterfest – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit, Attend Holiday Ceremony

Traits: Good, Romantic, Bookworm

Aspiration: Bestselling Author

Career: Writer (author branch)

Gen 12 Goals:

• Master Career (level 10) on main sim.
• Complete Aspiration on main sim
• Skills: Writing, one instrument of your choice, and Singing. (on main sim)
• Write as many books as possible – most of your main sim’s time should be spent writing any other time should be spent romancing their spouse.
• Fall in love with someone of a different “class” that is older than you.
• Your spouse should have a bad relationship with your extended family.
• Write the book of life and link it to your spouse. When your spouse dies, bring them back to life.
• DO NOT HAVE CHILDREN. You don’t have time for them, anyway.
• Your generation will end when both main sim and spouse have died of old age. Choose to have BOTH become ghosts and move on to the next partial generation!

Generation 12 Lots:

Gen 12.5: Unable to Say Goodbye (Victorian Era Part 1 1838 AD – 1849 AD)

Of note: This generation is listed as a partial generation simply because you’re using the same sim for this as you did for the last generation – this just happen to be a ghost this time. Next generation is, technically, the same sim again, but you will have different traits and (possibly) looks.

Your whole life was wrapped up in the one you love, and who said death had to change that?? When you and your love finally expire from old age, you move to the netherworld of Ravenwood, and manage to find jobs as Reapers thanks to the Grim Reaper’s compassion for your plight. Now your quest becomes to be reincarnated. Your only wish is to be able to start your life again, this time with a family that can appreciate you, and in a – hopefully – less spooky area of town.

Town: Ravenwood (Mourningvale)

Lot Traits: Private Dwelling, On Hallowed Ground, Romantic Aura

Lot Challenges: Off the Grid, Spooky

Holidays:

• Spring: St. Valentines Day – Give Flowers, Go on a Date, Romantic Spirit
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Winterfest – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit, Attend Holiday Ceremony

Traits: Lovebug, Romantic, Bookworm, Wise (if you can)

Aspiration: Ghost Historian

Career: Reaper (BOTH sims)

Gen 12.5 Goals:

• This generation BEGINS when your main sim dies of old age from the previous partial generation. At which point – so that everyone doesn’t know you’re sentient ghosts, you move to Mourningvale with your spouse and continue your life’s Journey.
• Complete the Reaper Career (main sim)
• Complete the Reaper Career (spouse sim)
• Become best friends with the Grim Reaper (main sim).
• You have vowed to never be separated from your “true love,” so always go everywhere together. Work, free-time, parties, whatever. Your two sims should always be together.
• Master the Thanatology skill (main sim)
• Master the Thanatology skill (spouse sim).
• Finish the Soul’s Journey on your main sim and prepare for reincarnation.
• Finish the Soul’s Journey on your spouse sim and prepare for reincarnation.
• DO NOT HAVE CHILDREN.
• ONCE BOTH sims are ready for reincarnation, you can pick (and/or make) families for them to be reincarnated into. The main sim’s family must live in Whispering Glen in Ravenwood, and the spouse’s prospective family must live anywhere BUT Ravenwood.
• Both your main sim and your spouse sim will get reincarnated as infants into their respective homes.
• Choose whatever traits and looks and relationships you want for the spouse sim, they are, in effect, getting lost in translation and are leaving the challenge.
• Your main sim’s reincarnated traits will be: Macabre, Chased by Death, and Gloomy. Remember: the next generation is starting as an infant, so no Aspiration yet! Also: remember, you are WELCOME to change your sims’ looks.
• If you choose, you can decide NOT to set the new family as your “parents” in the relationships.

Generation 12.5 Lots:

Gen 13: Reincarnation (Victorian Era Part 2 1850 AD – 1864 AD)

Of note: This generation is listed as a partial generation because you’ll be using the same sim for this “half” generation. This part of the generation encompasses your reincarnated sim from the age of Infant until they age out of Teenage years.

You have now been reincarnated – you thought – with your love, but where could they have gone? With your love nowhere to be found, and the Grim Reaper constantly breathing down your neck, where could you possibly go next? As you become a teenager, you realize the life you thought would be perfect… is not, and you vow to remove yourself from the world as you have always known it. Your only goal is to make enough money and squirrel it away so that as soon as you’re old enough you may move away from Grim’s influence on your life. The only job you can find is a part-time job at a Mausoleum, and you resent it every day you must work there.

Town: Ravenwood (Whispering Glen)

Lot Traits: Good Schools, Child’s Play, Teen Neighborhood

Lot Challenges: Off the Grid, Scare Seeker

Holidays:

• Spring: St. Valentines Day – Give Flowers, Go on a Date, Romantic Spirit
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Winterfest – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit, Attend Holiday Ceremony

Traits: Macabre, Chased by Death, Gloomy

Aspiration: Playtime Captain (child), Live Fast (teen)

Career: Handyperson (part-time as a teen)

Gen 13 Goals:

• Remember: your sim will be changing traits in this generation from last generation, and you are more than welcome to change what they look like. Even their family ties can be changed should you wish to!
• Grow up in a supportive and loving family, but with no contact with your reincarnated spouse. (They got “lost” in the transition!)
• May choose an after school activity as a child, but do remember, it must be completed (i.e. scouts or drama) by the time you get to be a teenager.
• Complete Playtime Captain Aspiration as a child (main sim).
• Complete Live Fast Aspiration as a teenager (main sim)
• Must have a part-time Handyperson career while a teenager (and get to rank 3 of the job).
• Avoid romantic Relationships as a teen this generation, you’re still feeling lost and confused that you cannot find your “true love” from last generation!
• Master Handiness as a teenager (main sim).
• The “next” generation begins when your main sim reaches Young Adulthood and moves out of their “happy” home.
• Give your main sim their final trait, and one of the three Vampire Aspirations (Master Vampire, Vampire Family, or Good Vampire – your choice).

Generation 13 Lots:

Before playing Generation 13.5, make sure to download (or make) a vampire who can turn your main sim and have the vampire live in a house somewhere in Forgotten Hollow. It might be helpful to have this vampire be high-ranking so that they will be able to train your sim later, as well.

Gen 13.5: Gothic Nightmare (Victorian Era Part 3 1865 AD – 1880 AD)

Finally old enough to move out, you take your stash of money, your obsession with flowers, death, and mortality, and you get as far away from Ravenwood as you can. You move to a small town deep in the country that no one has ever heard of, as far from Grim’s as you can get, hoping to be forgotten. There, you discover vampirism, allowing you to become a child of the night and live forever, free of Grim’s Influence for good. In this town, the darkness consumes you, and you retreat completely from the world. However, without your original love, you feel the need to replace their love with someone new, and you seduce someone new, and bring them into your world of forever darkness.

Town: Forgotten Hollow

Lot traits: Dark Ley Line, Vampire Nexus, Registered Vampire Lair

Lot Challenges: Off the Grid

Holidays:

• Spring: St. Valentines Day – Give Flowers, Go on a Date, Romantic Spirit
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Macabre, Chased by Death, Gloomy

Aspiration: Master Vampire, Vampire Family, or Good Vampire (your choice)

Career: Undertaker (Mortician branch)

Gen 13.5 Goals:

• Max the Flower Arranging, Pipe organ, Gemology, and Vampire lore skills on your main sim.
• Master the main Sim’s Undertaker career (Mortician branch).
• Cut off any connections with your parents after moving (contacting the rest of your family is at your discretion, but I suggest cutting all ties so that your secret doesn’t come out).
• Must seduce a young man/woman and fall in love with them (after becoming a vampire). You must then turn them (into a vampire) so you can be together for ever.
• Must become a master vampire.
• Electricity is now a thing – however power to homes is still incredibly rare. Continue to use the Off the Grid Challenge until directed otherwise.
• NO travel to anywhere outside of Forgotten Hollow this generation.
• Wait to have children until after your spouse is a vampire, as well. Yes, this means your children will be undead.
• Have at least 2 children.
• Become best friends with the vampire who turned you – they have almost become your surrogate parent.
• The heir must Max the Vampire Lore skill before moving out to start the new generation, and have made themselves a Vampire Cure potion (costs $1000 and can be made at any bar).
• Your heir’s traits will be: Rancher, Loves Outdoors, Horse Lover, and their aspiration will be a Championship Rider.

Generation 13.5 Lots:

Gen 14: Riding the Range (the American Old West – 1837 AD – 1895 AD)

You were born undead but you always had a respect for life. As soon as you could, you left your dark beginnings behind and became mortal. While your parents remained unmoving, never leaving their little hollow, you wanted to explore. So when everyone started talking about all the opportunities in the American west, you were on one of the first ships to America and joining a wagon train to find your destiny. You got yourself a homestead, and began doing what you had always wanted to – training horses. Without much in the way of money, you rescued everyone else’s cast-offs, and made them into amazing partners for their new owners. Your handiness keeps things working for far longer than they probably should, and your little ranch slowly became a haven for your animals and you began to think about the future. Becoming a member of the community, you get to know the locals, and finally find the woman of your dream at the local dance hall. Marrying and starting a small family, you make sure your child(ren) always know where you came from, so that they would never fall prey to the night.

Town: Chestnut Ridge (Galloping Gulch)

Lot traits: Great Soil, Bracing Breezes, Homey

Lot Challenges: Off the Grid, Wild Prairie Grass

Holidays:

• Spring: St. Valentines Day – Give Flowers, Go on a Date, Romantic Spirit
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Rancher, Loves Outdoors, Horse Lover

Aspiration: Championship Rider *does not need to be completed!

Career: Rescuing, training, and selling horses

Gen 14 Goals:

• The first thing you must do is become human. Drink that Vampire cure you brought with you.
• Being that you left home without your parent’s blessing, you must leave with only 20,000 – the only money you could squirrel away without them noticing. This is ALL you have to start your ranch!
• Max the Fitness, Horse Riding, Dancing, and Handiness skills, all on main sim.
• Rescue at least 10 horses during your lifetime, train and sell each for a profit.
• At least 3 foals must be born on your ranch.
• You must have at least three mini goats and sheep at any one time. (Any other animals are at your discretion.)
• You must win at least five endurance and 5 western pleasure competitions with your main sim, but you do NOT need to complete the Championship rider aspiration, as barrel racing didn’t exist yet, and jumping wasn’t a big thing in the old west.
• Once a week, you must head to the commercial district of your town and visit the local bar to dance and socialize. Your mate must be met here.
• Have at least one child.
• Make sure your child(ren) know the dangers of Vampires (teach them Vampire Lore to level 15 before they are a YA, so they could cure themselves if something unforeseen should happen!)
• Your heir’s traits will be: Genius, Self-Assured, Family-Oriented, and their aspiration will be Successful Lineage.

Generation 14 Lots:

Lot type Unlocked after this generation: Haunted House

Gen 15: Age of Spiritualism (Victorian continued 1870 (ish) AD – 1890 AD)

Your parent always told you horror stories about having been raised as a vampire. Their conviction that those creatures existed led you to believe in more than just the Vampire kind of supernatural. However, you feel that, to find those ghosts, you must be once again in the “Old Country”. Buying passage of the first ship you find, you take your inheritance and travel to the land or your ancestors, despite your parent’s objections. You find an ancient settlement and begin your search for the ghosts. You long to speak to them, to learn from them. In the process of learning to do this, you end up starting a business to help others get rid of their troublesome specters. Once you have an heir, you realize what a mistake you made, leaving home like that, and you become more and more focused on your heir, eventually losing touch with your other friends, and even your spouse in your quest to make sure your child won’t make your mistakes.

Town: Willow Creek (Pendula View)

Lot traits: Private Dwelling, Child’s Play, Good Schools (Lot must be set to “Haunted House” instead of Residential)

Lot Challenges: Off the Grid, Spooky, Cursed

Holidays:

• Spring: St. Valentines Day – Give Flowers, Go on a Date, Romantic Spirit
• Summer: None.
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal
• Winter: Christmas: Give Gifts, Grand Meal, Festive Lighting, Festive Spirit

Traits: Genius, Self-Assured, Family-Oriented (must also buy the Brave trait)

Aspiration: Successful Lineage

Career: Paranormal Investigator

Gen 15 Goals:

• Max the Parenting, Logic, Medium, and Vampire Lore skills (Vampire Lore should already be done when you start the generation) all on main sim.
• As mentioned above, your house must be a haunted house. Through this, you will meet Guidry, and he will help you get your license to become a Paranormal Investigator (DO NOT skip this step and buy the license from the Reward Store!).
• Earn enough points to buy the Brave trait – you are welcome to pick another aspiration (or more than one) to work on to get more points.
• Starting this generation, you are allowed to travel to areas other than your home neighborhood and the local commercial area. (Within reason – if it seems like that town would be too far away, you can still restrict travel)
• Have at least one child, and dote on them. Encourage good grades and values.
• When your heir is old enough to move out, divorce your spouse, leave them behind, and move with your child. (This will allow you to finish your Successful Lineage aspiration.)
• Your heir’s traits will be: Animal Enthusiast, Loves Outdoors, Family Oriented, and their aspiration will be Country Caretaker.

Generation 15 Lots:

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Updated: 12/3/25
(Adventure Awaits)

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Coming soon!

Coming Soon!

Coming soon!

Continuing with Version 1.0 until the rest of this page is done:

Once you’re ready to play, grab a copy of my Timeline Adventure Challenge Tracking Spreadsheet to track your progress!

Note on Lots: I will be building pre-built lots and putting them on the gallery with the tag “#timelineadventure” as I work through the challenge myself. My sims Origin tag is IllusoryThrall, feel free to toss me a follow. I will link each generation’s pre-built lots in boxes like this on this page for each generation – so if you’re not a builder, you can still easily play this challenge. I will eventually get to building lots for all generations, but for now it’s just the first few generations that I have completed. All lots mentioned on these pages are CC-free and playable! Also, if you build a lot that qualifies as those two things and want it included in these lists, please just drop me a comment here or a message at IllusoryThrall on the sims forums, I will check it out and add it if it fits!

Gen 8: Living With Lycanthropy (1400 AD – 1699 AD)

Living out in the countryside apparently comes with its own dangers. Just as you’re planning to set out on your own, your village is attacked by a mysterious wolf-like beast. Trying to save others and fight off this beast leaves you with a nasty wound. The local doctor can do little for you, and soon you find out why. You have become the beast you fought. In a panic, you retreat to the forest, attempting to hide what you’ve become. Slowly, you learn to live with your affliction, and, as you learn, you find others who have the same condition. The choice is now yours. Will you join them, or strike out on your own?

Town: Moonwood Mill

Lot Traits: Pick your own lot traits!

Lot Challenges: Off-the-Grid

Holidays:

• Spring: St. Valentine’s Day – Romantic Spirit, Go on a Date, Give Flowers
• Summer: Midsummer’s Eve – Art and Music spirit, Drinking, Fire, Party Spirit, Tell Stories
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal, Wear Costumes
• Winter: Christmas – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit, Attend Holiday Ceremony

Traits: Choose from the following for your first trait: Loner, Outgoing, or Party Animal, then your other two traits are up to you.

Aspiration: Werewolf Aspirations: starting with the Werewolf Initiate, you can then choose any of the following three: Emissary of the Collective, Wildfang Renegade, or Lone Wolf. (You may also attempt to complete more than one of these three.)

Career: None

Gen 8 Goals:

• Complete the Werewolf Initiate aspiration, then at least one of the following three: Emissary of the Collective, Wildfang Renegade, or Lone Wolf.
• Max the Athletic skill, as well as two others of your choice on main sim.
• Must always “Try for Baby”. Birth control is not a thing yet.
• Have at least one child – do not have to get married, but your child must live with you.
• Your heir’s traits will be: Good, Jealous, Paranoid, and your Aspiration will start with Werewolf Initiate.

Generation 8 Lots:

Gen 9: Stuart Era Justice (1603 AD – 1713 AD)

Growing up in the woods as you did, you came to fear the local “witches” and “beasts”, and – once you have figured out how to rid yourself of your parent’s beast form – you aspire to rid the world of the danger they pose through the legal system. You have a fascination with collecting things, and fill your home with the strange and exotic items you find while witch hunting. Your home also seems cursed by these “witches” and “beasts” – proof, in your mind, that they are dangerous and must be dealt with harshly.

Town: Willow Creek (Foundry Cove)

Lot Traits: Study Spot, Convivial, Mean Vibe

Lot Challenges: Off-the-Grid, Cursed, Gremlins

Holidays:

• Spring: St. Valentine’s Day – Romantic Spirit, Go on a Date, Give Flowers
• Summer: Midsummer’s Eve – Art and Music spirit, Drinking, Fire, Party Spirit, Tell Stories
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal, Wear Costumes
• Winter: Christmas – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit, Attend Holiday Ceremony

Traits: Good, Jealous, Paranoid

Aspiration: You start with the Werewolf Initiate aspiration, then complete the Cure Seeker Aspiration, followed by the Soulmate Aspiration

Career: Law

Gen 9 Goals:

• Complete the Werewolf Initiate Aspiration, followed by the Cure Seeker Aspiration on your main sim. Once you are human again, complete the Soulmate Aspiration.
• Complete the Law career – either branch on main sim.
• Skills to Max on your main sim: Logic, Research and Debate, and Charisma.
• Any Occult sims you know (Werewolf, Spellcaster, Alien, Vampire, or Mermaid) you must immediately become enemies with as soon as you are cured of lycanthropy – including your own family.
• Must always “Try for Baby”. Birth control is not a thing yet.
• Have at least one child.
• Your heir will have the traits: Good, Child of the Islands, and Child of the Ocean, and must choose the Beach Life Aspiration.

Generation 9 Lots:

Gen 10: Fins and Piracy (1650 AD – 1730 AD)

Your parents seemed to hate everything that wasn’t expressly human, and your only thought is escape from the pressure. Shortly after you came of age, you stumble across a position on a ship, and you take to the seas. As you rise in the ranks on the ship, soon you discover there is more to the sea than you ever knew possible. You become one of the denizens of the ocean, although you hide your fins from your crew, and you spend as much time as possible below the waves.

Town: Sulani (Oha’nali Town)

Lot Traits: Island Spirits, Sunny Aspect, Bracing Breezes

Lot Challenges: Off-the-Grid

Holidays:

• Spring: St. Valentine’s Day – Romantic Spirit, Go on a Date, Give Flowers
• Summer: Midsummer’s Eve – Art and Music spirit, Drinking, Fire, Party Spirit, Tell Stories
• Fall: All Hallows Eve – Remembrance, Spooky Spirit, Fire, Grand Meal, Wear Costumes
• Winter: Christmas – Give Gifts, Grand Meal, Festive Lighting, Festive Spirit, Attend Holiday Ceremony

Traits: Good, Child of the Oceans, Child of the Islands

Aspiration: Beach Life

Career: None

Gen 10 Goals:

• Become a mermaid. This must happen during your first week in the new generation, and can be done via Reward store Mermadic Kelp, or finding some Kelp on your own.
• Skills to Max on your main sim: Fitness and Mischief
• Complete the Beach Life aspiration
• Must always “Try for Baby”. Birth control is not a thing yet.
• Have at least one child.
• Your heir must be male and their traits will be: Perfectionist, Hates-Children, Noncommittal, and your aspiration will be Friend of the World. You must also cure your heir of Mermaid-ism (if they have it) before they take over as the next generation (take two Mermadic Kelps, then get in the water).

Generation 10 Lots:

Community Lots Unlocked after this generation: Museum (These became a thing in the early to mid 1700’s)

V2.0 Main Page | Gens 1-5 | Gens 6-10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Updated: 10/17/25
(Adventure Awaits)

V2.0 Main Page | Gens 1 – 5 | Gens 6 – 10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 40 | Gen 41 – 42

How to Use this Page:

Welcome to the Timeline Adventure! On this page, you will find the next five generations of the full 2.0 version of this challenge. Make sure to click on the tabs below each generation’s header so that you know all that you need to know to complete the generation! That being said, again, welcome… and Have FUN!

V2.0 Main Page | Gens 1 – 5 | Gens 6 – 10 | Gens 11 – 15 (WIP)
(V1.0) Gen 11 – 15 | Gen 16 – 20 | Gen 21 – 25
Gen 26 – 30 | Gen 31 – 35 | Gen 36 – 39 | Gen 41 – 42

Written by IllusoryThrall
Updated: 1/16/25 (through Life & Death)
Main Rules & Gens 1-9 Updated to Version 2.0 (through Adventure Awaits)
(Exception: the lot reference is still wrong right now… but I’ll fix it)

Note: This is under construction as of 8/7/2025. I will remove this notice when I’m done!
During this update, you may see discrepancies in the generation numbers!!
Note2: The Tracker is now in beta for this challenge, updated through gen 5!
You can find it -> here <-

I am adding a number of features and generations to this challenge, and unfortunately, the new way I’m setting up the challenge pages is very time consuming, so I can’t just copy paste everything in and have it work right away… so I will have to do it a little bit at a time. The first generation will not be changing, however, so if you’re going to restart the legacy, this is the PERFECT time to do it, as the additions I am making start as early as the SECOND GENERATION and will make the over-arching story make more sense. (I hope!) My goal is to do a little bouncing back and forth between ENSB 2.0 and Timeline 2.0 to give my brain breaks in-between, so please, bear with the process!! I WILL leave the FULL old rules up until I have fully completed the new rules! (So, yeah, there will be two rule sets for a while… sorry!!) Thanks for your patience! ~Thrall

Introduction to the Challenge:

Welcome to the Timeline Adventure Challenge! This is a story-based generational challenge that will take you through history from the Stone Age into the fantastical future. It is not for the faint of heart, as it spans nearly 50 generations. I based the rules off of having all of the expansion packs (excluding the Star Wars one) and I will be trying to keep this updated with new packs, but it would still be possible to complete if you’re missing some by either skipping the generations pertaining to the missing pack or changing the goals for that generation. Also: if you are too scared of the full 40+ generations, feel free to pick and choose which generations to play as you go (although you’d miss large parts of the story) and just have fun with discovering history. There is also a hefty dose of fantasy in this challenge, and it does include the Supernatural Occult states. The Sims game itself requires some imagination to play, and so does this challenge. If this isn’t up your alley, you could either skip the more fanciful generations or find a different challenge. This challenge follows a family dynasty that starts in Europe and eventually comes to the USA, so expect the history involved to follow that track, as well. This is not so much a building challenge as it is a game play and “Legacy” challenge, and, to that end, I will be providing lots I have built for each generation and era. You are NOT required to use them, however. I highly encourage building your own lots – I’ve had as much fun researching the architecture as I have playing the challenge, however, I didn’t want this challenge to be inaccessible to non-builders. The provided lots are linked from a greenish box at the end of each generation’s rules and will be filled out as I work my way through testing the whole challenge. I have also tried to make this challenge appropriate for all and as family friendly as possible, though I honestly would recommend this be played by people 14 years old or older. History was pretty brutal at times, and – since this follows history – this may not be for everyone! There will be death and woohoo, however, as those are things that really can’t be avoided.

One final note: this challenge truly is designed for storytellers at heart. If that storytelling means your story takes a different turn from what I wrote, THAT’S OKAY!! Mine is simply a suggestion. Also: if you want to use CC or mods, have at it. This challenge very much lends itself to be especially fun to play if you’re willing to get some mods or CC that will help you immerse yourself into the time period.

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