#HistoricalSims

[stereo-91]

MEDIEVAL CEILINGS BUILD SET

-1 MONTH EARLY ACCESS ON PATREON-

-PUBLIC ACCESS ON PATREON NOW-

First of ALL, we are terribly sorry for this long period of absence, we had study, work, complications, and thousands of things going on !!!

We have been working for the last week on these medieval ceiling ideas and medieval beams, and it came out as a mini amazing set which you can use to create a lovely wood cabin, or a great hall with these new medieval wood ceilings.

This Set Includes

5 Ceilings

3D Beams that you can place anywhere, as you like

4 Triangular Wall covers (For hiding exposed ceiling spaces)

 It's ALL BASE GAME Compatible, as usual !!

 Swatches in light, dark and colourful options !!!

 The ceilings are easier to place since they're wall sculptures and can be placed at your desired height. They are found in ceiling decor and wall sculptures in build/buy

One month early acces.

PUBLIC ACCESS NOW AVAILABLE...

LINK BELOW:

We Hope You Enjoy!

[theroyalhouseofwindenburg]

The Domino Effect

Following Dorthea's passing, The Dowager Queen Margaery's health declined. And by the winter of 1354, she was seemingly nearing her final days. Her bedchamber was filled with priests, nuns, and her closest family, as they all loyally stood by her side. Margaery sat up in her bed and called for her grandchildren. Princess Augusta first came to her, kneeling at her side.

"Augusta, you are a vision of grace and strength. I am so proud of the woman you've become," Margaery spoke softly, her eyes filled with love as she gazed at her granddaughter. "Your beauty is a reflection of your grandmother, Queen Anne. I see her spirit shining through you," Margaery continued, a hint of sorrow in her voice. "I am sorry for the pain caused by my son's actions against you, your mother, and our family. It weighs heavy on my heart."

"But do not let my passing hinder your path, Augusta," she urged, her voice gaining strength as she caressed her cheek. "Go to Tartosa, you are to be Empress one day, and let love and diplomacy mend what has been broken. Your future is bright, my dear, and nothing should stand in its way." With tears in her eyes, Augusta moved to the side. King Edward walked to his grandmother's bedside, taking her cold and frail hand into his. Margaery looked into Edward's eyes with a sense of peace, her hand trembling as she reached for her grandson's. "Edward, in your hands rests the crown's unwavering legacy. Let the realm feel your benevolence, as my Wilhelm once did, for kindness and devotion are the strongest swords," Margaery whispered weakly.

Edward clasped her hand gently, his eyes reflecting the weight of her words. "I will do my utmost, to honor both you and my grandfather's legacy. I pray that I can bring as much light to the realm as you both once did."

With a faint smile, Margaery continued, "Your grandfather would be proud, just as I am, for your reign shall mend the scars of your fathers mistakes. Seek a queen whose heart mirrors your resolve, for in her lies the future of our line."

Edward nodded solemnly, his determination shining through. "I will find a queen who shares our vision, one who will stand by my side as we steer our realm under the Watcher's guidance."

Margaery's voice grew softer, yet carried a firmness that belied her frailty. 'The crown must never falter, Edward, for it is the beacon that guides this realm,' she reminded him. 'I need to rest now for a while.' Her words were gentle, yet weighted with the knowledge of impending farewells. As Edward leaned in, she whispered to him, 'Remember always, I love you dearly."

In these moments, Margaery also imparted a crucial decision. The Kingdom of Effenmont, a jewel off the coast of Windenburg that had come into her possession after her father's passing years prior, would pass to King Edward upon her eventual departure, becoming a state of Windenburg. This gift, intertwined with her love and guidance, would forever shape the realm they both held dear.

As Edward gazed out the window at the falling snow, he felt the weight of centuries resting upon his shoulders, each snowflake a whispered reminder of the legacy he must uphold, the mistakes he must correct, and the future he must forge for his realm and his people.

In the early hours of the morning the following day, Margaery lay on her bed, her eyes fluttering open slightly as she weakly called out for Edward. He hurried to her side, his heart heavy with impending loss, yet he masked his emotions with a calm demeanor.

With a stern but loving expression, Margaery reached out for Edward's hand and whispered, "Do not forget what I've told you, The crown must never fall."

Edward nodded solemnly, his eyes reflecting determination and sorrow. "I won't forget, I promise."

As Margaery attempted to sit up, a sharp pain pierced through her chest, causing her to gasp. She cried out for a priest, her voice strained yet resolute. The priest rushed to her bedside, offering prayers and comfort as Margaery lay back, her breaths becoming shallower.

In her final moments, She whispered her late husband's name, a final farewell to the love of her life. "Wilhelm?" she breathed, her voice barely audible amidst the hushed room. Her eyes slowly closed, and the priest, after a brief examination, turned to the King with a somber apology, saying, 'I'm sorry, Your Grace. she has passed.' The room fell into a solemn silence, the weight of Margaery's legacy lingering in the air."

Edward stood by the foot of the bed, his gaze fixed on Margaery's frail form. The soft glow of candlelight danced across the room, casting a somber ambiance that mirrored the heavy emotions in Edward's heart. Though surrounded by loved ones and attendants, he felt an unyielding solitude settle upon him, as if the world had receded into a distant murmur, leaving only him and his grandmother in that final moment.

In the days that followed Margaery's passing, a wave of sorrow swept through the kingdom as news of her departure spread like wildfire. Citizens from all walks of life, from the bustling markets to the quiet countryside, made their way to Westsimster Abbey, their solemn faces a testament to the deep respect and admiration they held for their departed queen.

Inside the grand halls of the abbey, a scene of profound mourning unfolded. The royal family stood together, their heads bowed in reverence, as they surrounded Margaery's peaceful figure. She lay adorned in her finest regal attire, a testament to her grace and dignity even in death. Her robes, woven from the finest purple satin, cascaded around her in gentle folds, accentuated by the soft gleam of ermine furs that spoke of her regal lineage.

A crown, symbolizing her reign and legacy, graced her brow, its jewels catching the flickering candlelight and casting a radiant glow upon her serene features. Despite the weight of grief that hung heavy in the air, Margaery appeared as if she were merely slumbering, her expression one of tranquil repose. As Edward approached Margaery's resting place, his heart heavy with sorrow, he found solace in the memories of her unwavering strength and kindness. With a voice touched by emotion, he spoke to the gathered mourners:

"We stand here today not just to mourn the loss of a queen, but to honor the legacy of a matriarch whose love and wisdom guided us all. Margaery was not just a ruler; she was the heart and soul of our family, a beacon of grace and compassion in times of turmoil. Her absence leaves a void that can never be filled, but her legacy of unity and empathy will continue to inspire us as we navigate the path ahead. Let us remember her not with tears of sadness, but with gratitude for the light she brought into our lives."

Following her funeral, Margaery was placed in her coffin and carried beneath the grand halls of Westsimster Abbey. There, in the dim light of the crypt, she was laid to rest beside her late husband, King Wilhelm IV. The royal family gathered around her final resting place, their faces etched with grief as they mourned her one last time.

The chamber echoed with the soft sounds of weeping and whispered prayers, a testament to the deep loss felt by all. As the moment of farewell drew to a close, they began to exit the chamber, their hearts heavy with sorrow. King Edward lingered at the entrance, his eyes cast downward in despair. His mind was full of emotions, an immense amount of grief, responsibility, and reflection.

He thought of his grandmother's final counsel, the words that would forever resonate within him: "The crown must never falter." The weight of her legacy and the promise he had made felt almost overwhelming in that moment.

As he took his final steps out of the chamber, Edward whispered to himself, "I will not let you down, this crown shall never fall.".

Queen Margaery 1279-1354 (75 yrs)

May the Watcher guide her into the light ♡

[southernsimlish]

Hey

Just posting to say i'm not dead lol

[georgiapeachsims]

Years 1135-1145 of my Medieval Shipwrecked Save

[wewantmods]

30+ Sims 4 Medieval CC: Embark On An Epic Journey

Thanks to creators: @shimydim @Kennetha_v @Nemesis_im @plumbobsnfries @sifix @simbishy @oydis @melancholymaiden96 @remussirion @bluecravingcc @simmiev2 @historicalsimslife @lhonna @dissiasims @soloriya @philo @msqsimsofficial @kiolometro @arltos @nolcanol @simsbylinea @lady-moriel

[anothersimlishtragedy]

Old Willow Creek, 1882, Lady in Green

dress by @linzlu 

hat by @simverses 

fan by @janesimsten (pose is a part of the Regency mod, don’t ask just download it already)

[labuenosairesfrancaise]

Barcelo Palace

Hi Guys! I'm sharing the Barcelo Palace. 

Once a lavish household, it was converted into a highschool. 

It is located in Avellaneda, Buenos Aires, Argentina. 

The interior space is almost according to floorplan but I made some changes to make it more playable. 

The spaces are decorated for you to know what it is each space meant for, but you can modify to your own taste. 

You  will need lots of CC for it to work properly, mostly from Felixandre, TheJim, SYB, Aggresivve Kitty, among others.

Please let me know if you like it :)

Enjoy!

https://www.patreon.com/posts/81619315?pr=true

[nytil-sims-storybook]

Images persos - Characters’s pics

Bidonjour ! 

 Les screens de Hildegarde sont dispo gratuitement sur mon Patreon ! ;-)

------------------------------------------------------------

Hildegarde's screenshots are available for free on my Patreon ! ;-)

https://www.patreon.com/posts/77447681?pr=true

Kises !

[summerr-the-simmer]

Now that Mrs. Downing has passed, Cressida is in charge of managing the household. That, along with motherhood, takes up much of her time, but she manages to plan a tea for the young people. She hopes to match Cassandra with Mr. Kyleson, both because it is an advantageous match and because she'd like to keep him close to her. However, they do not seem to be hitting it off.

Shortly after the tea, she discovers that she is expecting again. She tries to avoid her matrimonial duties whenever possible, but there have been a few times that she did lay with her husband. The baby could be his, or Mr. Kyleson's. Perhaps she would never know.

[sims4utopia]

Meet Loretta Henning

Aspiration: Big Happy Family Traits: artistic, open-minded and elegant Career: Stay-at-home woman

[nonsensical-pixels]

i've been on a historical challenges binge recently, so have the fruits of that! starting off with: 3 new, long gowns for your stuck-in-the-past sims! they are each meant for different periods of history 🥰

i do plan to add on to this collection, as i've seen a lot of very cute hairs, accessories, etc. that ts2 doesn't have yet 👀 so keep an eye out! more info on all 3 dresses under the cut 👇

DOWNLOAD: SFS | MF ⌛

credits go to @my-historical-sims, @teanmoon, @clepysdra, and @zx-ta for the original ts4 creations! and to ea/maxis for the original mesh of the swan dress, which is technically a sims medieval to sims 4 to sims 2 conversion 🥰

ITEMS INCLUDED

4T2 MY-HISTORICALSIMS' MEDIEVAL BELTED DRESS (SFS | MF) - made as a late birthday present for @spell-bloom 😍 - mesh is yf-af only, but elder-enabled - everyday, formal, outerwear - 12 swatches - 5769 polys! 4T2 TEANMOON'S MINOAN MAIDEN DRESS (SFS | MF) - a redux of a dress i posted to the simscord literally a year ago and should never have posted tbh, the original was so bad - paired with 4t2 @clepysdra's gladiator sandals by me - meshes for tf-af, but again, elder enabled - everyday & formal - 6 swatches - 7190 polys! 4T2 ZXTA'S SIMS MEDIEVAL SWAN DRESS (SFS | MF) - expect some gaps between the cross-fabric at the back and the actual back, since they're painted on - mesh is yf-af only, but elder enabled - everyday & formal - 6 swatches - 3028 polys

SWATCHES

MEDIEVAL BELTED, MINOAN MAIDEN, AND LASTLY SWAN

if there are any issues that you find with this set, please don't be afraid to let me know! part 2 will come whenever i have the energy honestly, so don't get too excited. happy simming though, and when you download this, do keep in mind,

[stereo-91]

WIP

NOW AVAILABLE

-FREE ON PATREON NOW-

-MEDIEVAL VAULTED CEILINGS-

FREE LINK BELOW:

[theroyalhouseofwindenburg]

The Reaving: Part 2

The following morning was Christmas Eve, and snow fell lightly outside of Windenburg Castle. King Edward and his mother, Queen Cordelia, sat down for a meal in their private dining hall. Cordelia seized this opportunity to share her unsettling revelation from the previous night. The air in the chamber was quiet but heavy as she sat across from Edward at the long wooden table, where a simple spread awaited them, accompanied by warmed cider. Cordelia’s gaze was distant, her brow furrowed, lost in thought—a sight not unnoticed by her son.

Edward looked up from his empty plate, arching an eyebrow.

“Mother, you’ve barely touched your food. Is something troubling you?”

Cordelia glanced at him, her lips pressed into a thin line. She seemed to weigh her words carefully before speaking, her tone measured but edged with tension.

“I am troubled, Edward,” she admitted. “Last night, I witnessed something most unsettling.”

Edward, mildly intrigued, turned to her.

“And what might that be?”

Cordelia paused, gesturing toward the staircase before continuing.

“I saw Lady Adelaide in a most… distasteful display. She struck our maidservant Philippa, someone who has been with our family for years. She slapped her straight across the face, in fact. Then, in a voice as bold as sin, she announced that she would be queen and that Philippa should ‘remember her place.’”

Edward’s face softened, and he laughed, dismissing her words with a wave of his hand.

“Mother, surely you must be mistaken. Adelaide? A violent hand? She wouldn’t hurt a soul.”

Cordelia’s expression darkened.

“Are you calling me a liar, Edward?” she asked, her voice low and steady, simmering with hurt and indignation.

Edward jolted, taken aback.

“No, I only meant… she doesn’t seem the type.”

“Then I urge you, my son, to open your eyes,” Cordelia replied, her voice stern but laced with pleading. “Adelaide is more than you think she is, and not all of it is for the better.”

Edward looked down, considering her words. The flicker of doubt she’d planted deepened as he drifted into a silent, pensive gaze, the weight of his mother’s warning settling upon him.

The bitter winter winds cut through Bagley as Prince Harold fought alongside his men, his face bare and exposed to the frigid air. His helmet had long been given to a soldier who’d lost his own, but Harold moved through the chaos undeterred, his resolve fierce. Snow spiraled from the dark, brooding sky, mingling with the smoke of battle that billowed over the frozen fields. Amidst the frenzied clash of steel and cries of the wounded, Harold’s gaze fell upon a figure he recognized: Ser William Mason, one of his closest friends and fiercest fighters, lay motionless on the ground, his helmet lost.

A chill beyond winter’s reach settled over Harold as he raced toward him, his heart pounding with dread. He reached William’s side, fear gripping him as he pulled him up, throwing the weight of his friend over his shoulder. Shielding him from the blows of the enemy, he carried him to the edge of the battle and lowered him carefully behind the cover of a low stone wall.

William’s eyes fluttered open, his face ashen and dazed.

“Harry…” he murmured, a weary smile flickering as he recognized his friend. “You mad fool… you’ll get yourself killed for the likes of me.”

Harold knelt beside him, gripping William’s shoulder.

“There’s no way I’d let you die in the snow like a forgotten ghost,” he replied firmly. “You’re stronger than this, William. Hold on just a little longer.”

But before William could respond, his eyes widened, terror igniting in their depths.

“Harold—behind you!” he shouted, his voice raw and desperate.

Harold whipped around, his heart seizing as he saw the glint of steel—a soldier of Henford’s, sword raised, bearing down on them with murderous intent. Both men’s voices tore through the cold as they shouted, raising arms to shield themselves against the deadly blow as the shadow loomed over them.

That same night at Windenburg Castle, the royal family gathered in the Great Hall, feasting and celebrating the eve of Christmas. The hall was alive with laughter and lively conversation, candlelight casting a warm glow over tables laden with sumptuous dishes and the finest wines. Seated beside King Edward was Lady Adelaide, her gaze resting attentively on him as he spoke of his kingdom.

Their conversation drifted towards Edward’s alliances and the pressing matters of Windenburg’s security, each word a reminder of the weight that sat on his shoulders. As Edward spoke, his voice softened with rare vulnerability.

“When I see the toll this war has taken, the sacrifices made, it haunts me. These soldiers—they aren’t nameless pawns. They’re husbands, fathers, sons, all fighting for a land they call home. We, too, have a duty to shield them from such suffering.”

Adelaide’s brow arched, a faint trace of impatience flickering across her face as she sipped her wine.

“Edward, you’re their king, not their keeper. Worrying for those who choose to fight is… sentiment wasted. Our resources are better spent on Windenburg itself, wouldn’t you agree?”

Edward’s eyes narrowed slightly, a hint of unease flashing in his gaze, though he spoke patiently.

“And yet, their choice to fight is born of loyalty, of a desire to protect the lives they hold dear. Should we not, in turn, do what we can to honor such loyalty?”

Adelaide’s gaze hardened, her voice lowering to a tone as cold as the winter winds beyond the castle walls.

“Why waste resources on Bagley?” she said slowly, almost dismissively. “Their suffering is insignificant to us. We should focus on our own prosperity. After all, history remembers those who rise from the ashes, not those who save the fallen.”

Her words hit like a shockwave. The table fell silent, as though all the warmth of the hall had been smothered in a single breath. Even the distant laughter and music from the adjoining rooms faded. Heads turned, and all eyes locked on her.

Edward’s face turned ashen, anger burning beneath his steely gaze.

“You would speak so callously about a war that threatens the very bloodline of this family?” His voice rang with disappointment and fury. “My mother is of Bagley blood, and the royal family of Bagley is here at this table! You forget that these ‘insignificant’ lives are not just numbers; they are my people, and I refuse to turn my back on them. If you can’t see the humanity in this struggle, perhaps you should take some time to reflect.”

Adelaide’s face drained of color as she absorbed the weight of his words. Rising abruptly, she glanced around to see the unyielding stares of the court fixed upon her, their judgment heavy and unspoken. Her composure slipping, she turned and swiftly exited the hall, her footsteps echoing through the silence that lingered long after her departure.

In the early hours of Christmas morning, snow blanketed the battlefield, an eerie hush enveloping the war-torn landscape. The ongoing conflict had quieted for the night, and within the confines of his tent, King Henry lay in restless slumber. Arthur Cromwell, a trusted advisor to King Henry, entered cautiously, the chill of the night clinging to him like a shroud. He paused, letting his gaze settle on the sleeping king, before addressing him in a hushed tone.

“Your Grace,” he began, his voice a gentle summons piercing the stillness. “I apologize for waking you at this hour, but I’ve received a parcel of… unusual nature. It’s from Lord Rodrick.”

Henry blinked awake, confusion etched on his features as he adjusted to the dim light filtering through the canvas.

“Lord Rodrick? He sends gifts now?” A trace of suspicion laced his words, his gaze drifting to the chest resting by Arthur's feet.

Arthur nodded, a grave expression settling on his face.

“Indeed, Your Grace. It came with a note, but I thought it best to deliver it to you directly. Lord Rodrick is not a man given to idle gestures; this is either an offering of some kind or something meant to unnerve us.”

Nodding, Henry's expression darkened as he looked toward the note, his hand trembling slightly.

“Then let us see what Rodrick has deemed fit to share on this sacred morning.”

With a steady hand, Arthur opened the note, his brow furrowing as he read aloud:

“To The Illustrious, King Henry of Bagley, On this Christmas morning, I extend my warmest wishes for peace and reflection in a season devoted to family and the bonds that hold us. In the spirit of the season, I offer you a gift and, I hope, a source of clarity. True understanding often comes wrapped in unexpected forms, revealing the depths of what we hold dear. May this gesture serve as a reminder of the ties that bind, even in times of struggle, and bring you insight on this sacred day. With utmost sincerity, Lord Rodrick Henford.”

Both men stared at the note in silence, an icy dread filling the tent that no fire could dispel.

Henry's hands shook slightly as he crouched down, resting his fingers on the cold iron latch of the chest. He took a breath, steeling himself, and lifted the lid.

The lid creaked as it opened, and then—a stillness, followed by the sickening realization.

Henry’s face paled as his eyes fell on the contents, horror twisting his features. He stumbled back, gasping, his voice breaking. “No… God, no!” His scream shattered the silence, a cry of pure, guttural agony.

Arthur took an involuntary step forward, eyes widening as he glimpsed what lay inside. “Your Grace!—” he shouted, his own voice hoarse with shock.

Henry collapsed, hands clutching his hair, shaking uncontrollably. “My son…” His voice faltered, choking on the words. “They’ve taken him from me, Arthur. My boy… my only boy…” Henry cried, He sank to the floor, clutching his knees to his chest, his body trembling as despair overtook him. The world around him faded, leaving only the cold emptiness where his son had once been. Arthur knelt beside him, a hand resting on Henry's shoulder, trying to anchor him to reality. “Nothing matters now,” Henry whispered, his voice hollow. “Nothing can bring him back.”

[southernsimlish]

Updated St. Willow's -

In preparation for the new Life & Death EP I updated the church/boarding school! Available on the gallery tonight!

[georgiapeachsims]

Years 1065-1075 of my Medieval Shipwrecked Save

[jenplayssims]

Sims 4 “Oregon Trail” Challenge (BACC)

Inspired by playing Oregon Trail on the Switch recently with my family as well as the Homestead Challenge for Sims 2 by child_of_air, I wanted to create a historical build a community challenge (BACC) with references to the Oregon Trail game (ie, river crossings, death by illness, new pioneers arriving by wagon train, etc). The below are guidelines for play, many adapted from the Sims 2 challenge for use in Sims 4. Please consider these guidelines flexible and tweak them as you wish to fit your gameplay. This challenge was written with all packs in mind but can be played without them.

HUGE thanks to @antiquatedplumbobs for providing me valuable feedback and helping my idea really come to life! Also thanks to @cowplant-snacks​ for being a sounding board and providing feedback. This challenge wouldn’t be the same without either of their input and I am so grateful!

The Basic Rules 

1. There is no electricity, no running water, and no access to technology that wasn’t invented prior to the 1850s. You may wish to utilize the lot trait “off the grid” to aid with this, but this is not essential. As long as the home, decor, and most behaviors of the sims matches the time period, how restrictive you choose to be in your gameplay is up to you. “Close enough” is ok for this challenge.

2. Each member of your wagon party has a backstory to their lives, and many of them are trying to escape from the confines of the restrictive social order or begin a new life. However, the items they take with them will be restricted to what their social rank was when they left. Space on the wagon is limited, and only the most precious items would be taken along. (More on items below)

3. At the start you will play your aspiring pioneer household as they journey by wagon to their destination, facing obstacles along the way. Once your pioneers arrive at their destination, they will all move into a boarding house with a host sim. Only the host household (which includes your first set of pioneers) will be played at this point. Once sims move out and begin their own homesteads, the neighborhood will be played in rotation. Each house will be played for 1 week (length of rotation of your choosing. 1 week is my recommendation).

4. Only the host or hostess at your destination will be able to have a job at first, which will be in politics. Everyone else will have to focus on developing their skills, adding to their hope chests, and preparing for their own homesteads. Sims cannot marry or move out of the boarding house until they have produced enough goods to begin their own homesteads.

5. Please note that your end destination does not have to resemble Oregon. The Oregon Trail game was simply an inspiration for this challenge.

Time 

The concept of time passing is up to you. You may want to let the seasons dictate the years, or you may want to base your year around a biological marker, such as the sim age spans. Some may want to make their own metric for years (ie, 4 days = 1 year). You may choose to not bother with the passage of time at all. If you choose to advance the passage of time, you will need to keep track of advancing technology (I recommend Decades Challenge for inspiration). This challenge could be played as a prequel to the Decades Challenge.

Getting Started

1. Create your wagon train lot for your pioneers to live on as they travel to their new home. You can build this yourself or pull a lot from the gallery (my recommendation is Oregon Trail Camp by HistoricalSim). If building your own, this functional tent looks like a covered wagon - http://simfileshare.net/folder/183978/ kindly hosted by @cowplant-snacks, amazingly made functional by @superflare, original by inabadromance.

2. Host Sims and House - Before the pioneers’ journey is complete, you will need to create a host house and a host/hostess sim. (Note: This step can be done right at the start or can wait till their journey is almost over.) Create a host sim of your choosing. This will be the only sim in the initial household able to hold a job, which should be in politics. The host will be the one to hand out homestead deeds (though not literally). The wagon load of pioneers will begin their new life here as they gather supplies and build up their skills to qualify for a homestead of their own. Consider it a boarding house of sorts and build accordingly. You’ll want space for many sims as well as skilling/crafting items available for use. 

3. Townies - Your game should have as few townies as possible to begin with as your first pioneers should be part of the town’s founding. You may use mods to prevent the game from spawning townies or you may create your own and use mods to make them fill the roles the game would normally spawn new sims for (mailperson, bartender, etc). You can also allow the game to spawn as it needs to and either ignore those sims or make them over to fit the historical context. (Note: The Sims 2 Homestead Challenge mentions creating Native people to serve as existing townies. This is up to the player)

4. Create your first wagon of settlers

a. Roll a dice to see how many are on the wagon (1-7, unless you use mods to increase the household sim limit). They can be teens-adults. If you want to roll for gender, age, traits, etc you may. You can start with a married couple or single sim if you wish, but keep in mind that not all sims are guaranteed to survive the journey so more sims may be better for this challenge.

b. For each sim, roll their socioeconomic background: This determines the quality and quantity of items each sim may have brought with them to begin their new life/homestead. Note: Sims 4 furniture is stored in the shared household inventory, so may want to roll and make note of this somewhere but not actually choose the items until the sim has moved to their own homestead. 

1-2: Indentured Servant or Former Slave (2 Items, poor quality) 

3-4: Lower Class (5 Items, poor quality)  

5: Lower Middle Class (6 Items of poor quality and 3 items of medium quality)  

6: Middle Class (10 items medium quality)

c. Likewise with animals - it stands to reason that some would have brought livestock or perhaps a pet with them, but as these won’t really come into play until the sim moves to their own land, you can decide what they have now and then add them later.

5. Move them into your wagon train lot and begin their journey!

Optional: You can use my save file as a starting point for this challenge. It contains a wagon camp (Oregon Trail Camp by HistoricalSim) placed in Willow Creek. It also has the calendar already set up to include events on the journey and holidays (more on the journey and calendar below). Host house and sims are not included. http://www.simfileshare.net/download/4024989/

The Journey:

Your wagon of pioneer sims will begin their journey in spring. Their goal is to reach their end destination before winter begins. The length of this stage is up to the player - you may want to drag out the survival struggle or you may want to zip through it quickly. The average time of travel was 150 days. I’ve included a sample calendar below from my save file. The Oregon Trail begins in Missouri and ends in Oregon, and typically took months to complete with many hardships along the way. Any sim who becomes sick while on the journey will need to have a dice rolled for their survival odds (even - they live, odd - they succumb to their illness and die along the trail unless they are within a day of a Fort where they can purchase medicine). Also along the way are 4 river crossings (Kansas, Big Blue, Green, Snake) as well as passage through the Blue Mountains near the end. There are also 4 random events in the spirit of the original Oregon Trail game. For each of the 5 major events (spaced however the player chooses), roll a dice for their odds of success. 

1-3 unsuccessful attempt at crossing - roll to see which sim doesn’t make it

4-6 successful crossing - continue on

For the 4 random events on the calendar, roll a dice to determine which sim will be affected by the event. Roll the dice again for survival odds - if a 3 is rolled, your sim dies. 

Once the events are completed, the wagon arrives at the boarding house and moves in temporarily until their own homestead can be secured.

The sample calendar below from my save file includes all 5 events spaced out as well as a couple of stops at Forts where supplies can be purchased (medicine, food if you’re playing using the Simple Living lot challenge). I also included 4 random events and a few holiday celebrations.

Optional: If you’d like to further simulate pioneers journeying across the country, you can move your pioneer sim household to wagon camps in different worlds with each river/mountain crossing. If you’re using my save file, use the numbered wagon train lots as listed below.

Recommended worlds to use:

Kansas/Big Blue River Crossings - #1 stay on original lot in Willow Creek

Green River Crossing - #2 Henford

Snake River Crossing - #3 Oasis Springs

Blue Mountains Crossing - #4 Copperdale

Homesteads:

In order to qualify for a homestead, sims must gain 4 skill points in 3 different skills (Baking, Cooking, Cross Stitch, Fishing, Fitness, Flower Arranging, Gardening, Gourmet Cooking, Guitar, Handiness, Herbalism, Horse Riding, Juice Fizzing, Knitting, Nectar Making, Painting, Piano, Pipe Organ, Violin, Writing) as well as meet the qualifications for homesteads below:

Basic Homestead: all skills obtained, $100 starting fund, 10 household wares

2 Bedroom Homestead: all skills obtained, $200 starting fund, 12 household wares

3 Bedroom Homestead: all skills obtained, $300 starting fund, 20 household wares

Middle Class Homestead: all skills obtained, $400 starting fund, 30 household wares

If sims decide to marry, they must each obtain the skills individually but can pool household wares and money to qualify for a homestead. 

Since work is not allowed for the pioneers until they move out, they will need to grow and sell produce or create and sell crafted items to earn money. Items can be sold through their inventory for ease if desired. If using Chestnut Ridge as their town, items can also be sold at the General Store.

Household wares include what they rolled from earlier based on their socioeconomic backgrounds as well as anything they create while in the host house.

Note: if you choose to play with the Simple Living lot challenge turned on, you will also want your sims to bring some produce, canned goods, and possibly seeds with them to their homestead.

Once in their own homesteads, they can expand as they have funds and need or can move to a new lot.

Optional: When two homesteads have been established, you can build a Trading Post. This is where your sims can sell their wares through the sales tables available in Sims 4. A grocery stall from Cottage Living may also be placed. They can also sell items at the General Store in Chestnut Ridge.

If you prefer a lot from the Gallery, I highly recommend Old Western Township built by antiqueplumbobs (antiquated plumbobs : Western Township - Simblreen Gift #1 A CC-Free... (tumblr.com) It is perfect as a community lot for this challenge.

When all pioneer sims from the initial wagon have moved into their own homesteads, a second wagon of pioneers can be created and start their journey. As your initial sims have families of their own, you may choose to create families to journey to your town rather than individual sims. The second (and any future) wagon train households created will be played in rotation with the homestead households established by your original pioneers.

Careers:

Once on their own established homesteads, your sims can begin careers. 

At home careers: farmer, orchard owner, florist, woodworker, dairy farm, llama farm, chicken farm, horse breeder, goat herder, sheep farmer, nectar maker, juice fizzer, herbalist

Careers in game: fisherman, manual laborer, gardener, painter, politician, writer, lawyer, doctor, teacher, criminal, entertainer (Note: I would suggest creating a specific sim to be the doctor to unlock medicine, creating a teacher to be part of a wagon train once your town begins to have infants/toddlers, etc - add the careers as it makes sense for your town, as most making this journey initially would have been farmers).

Optional careers:

Create a clergyman to perform marriage ceremonies among the settlers. Can add a fee to their household funds for each marriage performed, etc.

Add in custom careers, such as Fur Trader ( Peebs : Fur Trade Career | Original Career This career... (tumblr.com) )

That’s it! See how far your town can grow and advance as new settlers arrive but most importantly, have fun!

PDF link to rules