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100% Achievement Guide
By SecretAgentAu
Guide for all 83 achievements (including DLC achievements) in The Oregon Trail.

NOTE: Guide is work in progress as I work through the last few achievements.
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Created by
SecretAgentAu
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Category: Achievements, Secrets, Walkthroughs
Languages: English
Posted
Updated
29 Sep, 2023 @ 7:11am
28 Sep, 2024 @ 8:27am
855 Unique Visitors
34 Current Favorites
Guide Index
Overview
A Fistful of Greenbecks 
A Good Cause 
Abigail Scott Duniway 
All Your Fish in a Roe 
Antiques 
Back and Forth 
Behind the Name 
Bet the Ranch 
Big Blue River 
Bison 
Cashing In 
Chasing Rainbows 
Columbia River 
Cooling Down 
Count Your Fingers 
Dare Go Hollow 
Douse the Fire 
Fact or Fiction 
Fettuccine Western 
Fish Story 
Flying Like a Bird 
Follow the Stars 
Fool Me Twice 
Fort Boise 
Fort Hall 
Fort Laramie 
Frail Moment 
Give a Man a Fish 
Going for Gold 
Gold in the Veins 
Golden Sunset 
Gold-Fashioned 
In Good Taste 
In the Pursuit of Knowledge 
Independence 
Independence Rock 
James Beckwourth 
John Jacob Astor 
Lewis and Clark 
Living Despite It All (WORK IN PROGRESS) 
Making Her Mark 
Marcus Whitman 
Meek as Moses 
Midas Touch 
Oregon City 
Pacific Railroad 
Pawnee Villages (WORK IN PROGRESS) 
Peperony and Chease 
Peppard's Folly 
Performing Sturgery (WORK IN PROGRESS) 
Play Right 
Putting the Band Together 
Rendezvous (WORK IN PROGRESS) 
Robert Newell 
Rufus Porter 
Sager Orphans 
Sail On! 
Shooting Hoops 
Sing-along 
Skillful 
Sky High 
Slippery as an Eel 
Smithereens 
Sob Story 
Spice of Life 
Take Your Chances 
Taking Credit 
Television 
Texas Fever 
That’s a Paddlin’ 
The Last Spike 
The Oregon Trail (2009) 
The Oregon Trail (2021) 
The Peoria Party 
The Real Work Begins 
Thief in the Night 
Trail Food 
Trail Mortality 
Trail Wildlife 
Wagons 
Winter (WORK IN PROGRESS) 
You Can't Eat It 
You have died of dysentery 
Comments
A Fistful of Greenbecks
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Win $100 or more in total from the Gunslinger's challenges

Prerequisite: N/A

Walkthrough: The Gunslinger offers 5 challenges as random events: speed, judgement, accuracy, nerve, and player's choice (replay a previous challenge).
  • Speed: 6 boxes will appear at the bottom of the screen to select. 5 will say “Miss” and 1 will say “Hit”. You must hit it faster than the timer or it will automatically miss.
  • Judgement: Wait for the referee to say “Go” before you shoot. He will say random other things such as “Oh I think I left the kettle on” before saying “Go”. You must hit it faster than the timer or it will automatically miss.
  • Accuracy: For this one, pick your best shooting skilled party member and hope they have high enough skill to win. You can make a lot of money on this one if you keep allowing the Gunslinger to double your money. DO NOT cash out early or you will not get the achievement.
  • Nerve: Pick a party member with high wit, and view each bottle until you see the message change to something like: “Gunslinger narrows his eyes”, “… frowns slightly”, etc.
  • Player's Choice: The fifth challenge is up to you to pick one of the previous 4 challenges to play again.

Tips: Cumulative on all playthroughs. The Gunslinger will double your earnings if you beat his challenge.
A Good Cause
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Make sure Lewis Southworth keeps all the money from his performance

Prerequisite: Bring Lewis a fiddle.

Walkthrough: Take the southern route after the Three Island Lookout on the 3rd leg of the journey. Before crossing The Snake River a second time, there will be a salesman with a fiddle for sale. You can negotiate the price as low as $20 depending on your choices and party wit/personalities. When you deliver the instrument to Lewis and watch the performance, he will attempt to pay you back the price of the fiddle. Decline to allow him to pay you back.

Tips: If you receive an IOU for the fiddle, Lewis will have to pay the IOU, and thus you will not earn the achievement.
Abigail Scott Duniway
Journey: N/A

Goal: Collect 50 Gallery items

Prerequisite: N/A

Walkthrough: Complete the daily contract and community railroad to earn 3 tokens and 4 tokens respectively.

Tips: Use those tokens to purchase artwork for 1 token each. That's the quickest way to reach 50. If you pick the correct railroad and complete the contract each day, it will take 2 weeks to reach 50 tokens.
All Your Fish in a Roe
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail

Goal: Catch every trophy fish

Prerequisite: N/A

Walkthrough: While fishing, there is a chance for some fish to appear with red sparkles. Those are trophy fish. There are 80 types of fish in total, and each one produces a rare chance for a trophy fish.

Tips: The community events have a daily fish that has a 20% increased chance of the fish appearing. This is very helpful for targetted fishing, as the trophy fishes are more likely to appear as well.
Antiques
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Deliver an antique to Oregon

Prerequisite: Complete “The Oregon Trail” journey to unlock the grandfather clock.

Walkthrough: This clock can only be bought in Independence and must be carried all the way to Oregon City.

Tips: I would recommend trying not complete any other quests that require carrying something at the same time as the antique clock. Additionally, focus on carrying wagon grease (so the wagon doesn’t break) and pelts (so that you can cross rivers), avoiding damaging the clock.
Back and Forth
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Witness a filla-ma-loo bird

Prerequisite: DLC required to unlock “Story” campsite waypoints

Walkthrough: Stay at a “Story” campsite waypoint for a chance to unlock this random event.
Behind the Name
Journey: The Chisholm Trail (DLC)

Goal: Meet Jesse Chisholm

Prerequisite: DLC required to unlock “The Chisholm Trail”

Walkthrough: Prior to leaving San Antonio, select "Talk" and then select "Jesse Chisholm" to speak with Jesse.
Bet the Ranch
Journey: The Chisholm Trail (DLC)

Goal: Reach Abilene with excellent cattle condition

Prerequisite: DLC required to unlock “The Chisholm Trail”

Walkthrough: As you progress through this journey, your decisions will impact the cowboys and subsequently the cattle herd. In random events, choose the option that does not split up the herd in any way. At the campsites, make sure to take care of your cowboys (cook their favorite meal and talk to them).

Tips: Bonus if you have the Cook class character already unlocked, as they cook better food, although this can be achieved without a Cook.
Big Blue River
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Cross the Blue River safely

Prerequisite: N/A

Walkthrough: Make it to the second waypoint after leaving Independence.

Tips: There is also no ferry at the Blue RIver, so you will have to ford or caulk your wagon. Save up the pelts you receive before crossing the Kansas River. There is only one waypoint in between the Kansas River and Blue River to obtain more pelts, and it may not be a hunting spot.
Bison
Journey: All except The Tranquil Trail, Lost Hollow, Rendezvous, White Water, and A Fur Trade

Goal: Collect 1,000 animals

Prerequisite: N/A

Walkthrough: Click on 1,000 animals while the party is traveling.

Tips: Cumulative on all playthroughs. You can enable the accessibility setting to auto-click on animals (highly recommended on Steam Deck, or if playing with a controller).
Cashing In
Journey: The California Trail

Goal: Sell at least 25 gold nuggets to an Assayer

Prerequisite: N/A

Walkthrough: At the cities, there is an Assayer available in Services that will exchange your gold nuggets for money. Sell a cumulative total of 25 nuggets.

Tips: Cumulative on all playthroughs. All Assayers offer different prices for the nuggets and can be haggled with. Haggling with a party member who has the “Charming” personality trait will increase the price more than a high-wit party member.
Chasing Rainbows
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Catch a Yellowfin Cutthroat Trout

Prerequisite: N/A

Walkthrough: Yellow Cutthroat Trout appear in the fishing waypoints on the Desert, Snake River Valley, or Mountains.

Tips: The Yellow Cutthroat Trout is considered one of the more uncommon fish types to catch. You will have an increased chance of catching this fish on the "Oregon or Bust" journey than the other two.
Columbia River
Journey: White Water

Goal: Earn 10,000 points in "White Water Rapids"

Prerequisite: N/A

Tips: Just keep trying until you get it. It takes a couple of tries not to smash into rocks too many times. You have two smashes, and on the third your wagon breaks.
Cooling Down
Journey: The California Trail

Goal: Use medicine to heal a Burned character completely

Prerequisite: N/A

Walkthrough: Use a party member with low composure to place the nitro at a mining waypoint. There is a chance the nitro will not explode. There is a chance upon replacing the nitro, it will explode with the party member close to the nitro, and they will be injured by “Burns”. Use your medicine to heal them (takes roughly 6 bottles of medicine to fully heal the burns).

Tips: Do not have a Prospector in your party, as they lower the chance of the nitro accidentally exploding.
Count Your Fingers
Journey: The California Trail

Goal: Use Nitro at least 12 times on the California Trail

Prerequisite: N/A

Walkthrough: Purchase or trade for nitro, and then use the nitro instead of digging at the mining waypoints.

Tips: Party members with high composure are more likely to place the nitro correctly. Party members with low composure have an increased likelihood of the nitro not igniting at all, or igniting as they are approaching to adjust it, which can injure or kill the party member. Prospectors lower the risk of nitro being mishandled, and lower the risk of the wagon jolting the nitro and causing an explosion.
Dare Go Hollow
Journey: Lost Hollow

Goal: Complete Lost Hollow in fewer than 15 days

Prerequisite: N/A

Walkthrough: (Note: There are many ways to play this, however this is the only way I've found to get this achievement.) The game starts on June 24th. On June 28th, a scout from the Moses party will inform you your rescue is 25 days away. The only constants in this game is that a train of survivors will arrive on July 3rd, and July 8th. When a train arrives, that whole day is skipped. You will need to spend from the 24th to the 28th balancing food supplies and keeping your survivor numbers high for when the 28th hits. You will gain the scout as a survivor on the 28th. From the 28th through the 3rd, balance between food supplies and aiding rescuers. Ignore Meek's party, they can survive starvation for a few days (at least 3), and redirect snakebites from Meek to anyone else by having them suck out the venom. One the 3rd hits, so long as you can get the rescue countdown to hit 0 on or before July 8th, let the survivors starve if you have to in order to make sure Meek survives.

Tips: Going to be honest, you are at the mercy of the RNG on this one even if you’re a skilled player. You’re going to need to be rescued no later than July 8th to unlock this achievement. I recommend ignoring basically every stat for your main party except for their food supplies. Meek is the only party member that matters, so if you have to lose the others for him to survive, so be it.
Douse the Fire
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Talk the Gunslinger out of his quest for vengeance

Prerequisite: N/A

Walkthrough: Complete each of the Gunslinger's 5 challenges (speed, judgement, accuracy, nerve, player's choice), and after the 5th challenge you will have the chance to talk him down.

Tips: Have someone in the party with high wit or with the “Charming” personality trait for a high chance of success.
Fact or Fiction
Journey: The California Trail

Goal: Become lost while searching for the meteorite

Prerequisite: Start John Evans’ quest “Wish Upon a Star”

Walkthrough: Randomly towards the end of the trail, there will be a chance to search for the meteorite.

Tips: Select a member with mild level wayfinding for a higher chance of becoming lost.
Fettuccine Western
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Win at all 5 of the Gunslinger's challenges

Prerequisite: N/A

Walkthrough: Complete all 5 of the challenges for the Gunslinger successfully. The challenges are as below:
  • Speed: 6 boxes will appear at the bottom of the screen to select. 5 will say “Miss” and 1 will say “Hit”. You must hit it faster than the timer or it will automatically miss.
  • Judgement: Wait for the referee to say “Go” before you shoot. He will say random other things such as “Oh I think I left the kettle on” before saying “Go”. You must hit it faster than the timer or it will automatically miss.
  • Accuracy: For this one, pick your best shooting skilled party member and hope they have high enough skill to win. You can make a lot of money on this one if you keep allowing the Gunslinger to double your money. DO NOT cash out early or you will not get the achievement.
  • Nerve: Pick a party member with high wit, and view each bottle until you see the message change to something like: “Gunslinger narrows his eyes”, “… frowns slightly”, etc.
  • Player's Choice: The fifth challenge is up to you to pick one of the previous 4 challenges to play again.

Tips: If you do not have $10 or more with you, you will not be able to accept the Gunslinger's challenges.
Fish Story
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Witness a Flambeau ambler

Prerequisite: DLC required to unlock “Story” campsite waypoints

Walkthrough: Stay at a “Story” campsite waypoint for a chance to unlock this random event.
Flying Like a Bird
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Have a unique encounter while traveling with a wind wagon

Prerequisite: Complete Peppard’s Folly to unlock the Wind Wagon.

Walkthrough: While using the wind wagon, there is a rare chance of a unique random event occurring in which an NPC will comment about the wagon.

Tips: This achievement requires using the wind wagon over and over until a rare random event occurs (it took me 6 runs on just the wind wagon to finally get the event to occur).
Follow the Stars
Journey: The California Trail

Goal: Listen to John Evans's story

Prerequisite: N/A

Walkthrough: John Evans is found before reaching Humboldt Wells as a random event. He offers to exchange $20 for a map of the location of the meteorite.

Tips: If you don’t have $20, you cannot start this quest.
Fool Me Twice
Journey: The California Trail

Goal: Receive Fool’s Gold 2 times throughout your journey

Prerequisite: N/A

Walkthrough: On the trail, there is a random event that appears in which a party or person will ask to trade the gold nuggets they have for some of your supplies.

Tips: A Prospector will be able to identify Fool’s Gold, but if they do, you will not get the option to receive it. Without a Prospector in your party, usually one party member will comment that the deal is too good to be true (e.g.: 6 gold nuggets for 20 bullets). You can haggle to lessen the damage since you will essentially be giving away supplies.
Fort Boise
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Discover Fort Boise

Prerequisite: N/A

Walkthrough: Fort Boise is at the end of leg 4 (Independence to Fort Kearny, Fort Kearny to Fort Laramie, Fort Laramie to Fort Hall, Fort Hall to Fort Boise).
Fort Hall
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Discover Fort Hall

Prerequisite: N/A

Walkthrough: Fort Hall is reached at the end of Leg 3 (Independence to Fort Kearny, Fort Kearny to Fort Laramie, Fort Laramie to Fort Hall)
Fort Laramie
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Discover Fort Laramie

Prerequisite: N/A

Walkthrough: Make it through the first two legs (Independence to Fort Kearny, Fort Kearny to Fort Laramie).
Frail Moment
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Make sure Little Mary gets a doll for her birthday

Prerequisite: Attempt to help the family with the broken-down wagon that appears as a random event.

Walkthrough: When you meet the family again at another random event where they ask for help making the doll, agree. Achievement will unlock before the end of the game.
Give a Man a Fish
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail, The Chisholm Trail (DLC)

Goal: Trade away a total of 500 pounds of fish

Prerequisite: N/A

Walkthrough: At all stopping points it is possible to trade fish for money. The normal price of fish is $1 per fish, but can be negotiated to $2 per fish with high enough wit or the “Charming” personality trait. Catch 500 fish and trade them for money.

Tips: Cumulative on all playthroughs. Additionally, fishing will not net the full amount fished unless you have a knife in your inventory (earned by completing the “Bitter Winter” journey).
Going for Gold
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Collect all 10 Dragoon medallions

Prerequisite: N/A

Walkthrough: You will need to reunite the Dragoons on 10 different playthroughs, and keep their medallions with you until you reach the 10th one.

Tips: Do not trade away or lose any of your Dragoon Medallions, as that will cause the journey to not count towards the 10 you need. Please click HERE to view the guide on how to convince each Dragoon to rejoin.
Gold in the Veins
Journey: The California Trail

Goal: Have the party activate Gold Fever

Prerequisite: N/A

Walkthrough: Keep mining/exploding gold mines at the waypoints until you receive enough to activate gold fever. Should take approximately 10 gold nuggets.
Golden Sunset
Journey: The California Trail

Goal: Arrive at Sutters Mill in California

Prerequisite: N/A

Walkthrough: Finish The California Trail with at least one party member alive.

Tips: The party doesn’t have to be in good condition, they just have to be alive.
Gold-Fashioned
Journey: The California Trail

Goal: Trade supplies for gold nuggets 3 times on the trail

Prerequisite: N/A

Walkthrough: On the trail there is a random event that appears in which a party or person will ask to trade the gold nuggets they have for some of your supplies.

Tips: Cumulative on all playthroughs. I normally see this about once per journey run, so it may take a bit to get 3 trades. Keep food and bullets stocked in your wagon to trade with. There is also a chance that the traders may offer you Fool's Gold instead, but the only way you will be able to tell is if you have a Prospector in your party. There is also an achievement for being swindled by Fool's Gold twice.
In Good Taste
Journey: The Chisholm Trail (DLC)

Goal: Cook a cowboy's favorite dish

Prerequisite: DLC required to unlock “The Chisholm Trail”

Walkthrough: Each cowboy has their own favorite dish (which changes each playthrough). After talking to them at several cooking campsites, they will inform you what their favorite dish is.

Tips: Alternatively, if you cook different dishes each time you stop, you will hit one of their favorite dishes faster than waiting for them to tell you.
In the Pursuit of Knowledge
Journey: The California Trail

Goal: Make a donation to the museum

Prerequisite: Start the quest “Wish Upon a Star” with John Evans.

Walkthrough: On Leg 3 of the journey, you will come across a random event to search for the meteorite that John Evans told you about. Keep searching until you find it (it may take several tries). Once you acquire the meteorite fragment, you will have the option to sell it, donate it, or keep it. Pick donate.
Independence
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Reach Independence

Prerequisite: N/A

Walkthrough: Play the Prologue.
Independence Rock
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Reach Independence Rock before July 4

Prerequisite: N/A

Walkthrough: Independence Rock is the waypoint after Fort Laramie, the first stop on the 3rd leg of the trail.

Tips: Try to keep the party moving at “strenuous” speed, and the achievement should be easy to unlock. If you can complete the first two legs in less than 30 days, you have 4 days to reach Independence Rock after leaving Fort Laramie.
James Beckwourth
Journey: Tall Tales

Goal: Win against Beckwourth in "Tall Tales"

Prerequisite: Complete the “Winter Migration” journey to unlock.

Walkthrough: James will challenge Moses to see who will bring back the most pelts in a 1 leg journey to Pawnee Village. You will have the ability to hunt beavers at hunting waypoints, trap beavers at trapping waypoints, or exchange pelts for bullets/traps/meat.

Tips: In all of my playthroughs, it appears that James will only ever bring back 34 pelts. If you find yourself in need of haggling, the carpenter in the party has the "Charming" personality trait.
John Jacob Astor
Journey: All except The Tranquil Trail, Lost Hollow, Rendezvous, White Water, A Fur Trade

Goal: Spend a total of $20,000

Prerequisite: N/A

Tips: This is cumulative on all playthroughs. The easiest way to spend lots of money on each journey is to start with a smaller wagon, catch lots of fish, and then haggle their price to $2 each to sell them. Then buy bigger wagons further along the trail when they are more expensive.
Lewis and Clark
Journey: All except The Tranquil Trail, Lost Hollow, Rendezvous, White Water, A Fur Trade

Goal: Travel 8,000 miles

Prerequisite: N/A

Walkthrough: Cumulative on all playthroughs. The Oregon Trail is 2,170 miles (or more depending on which routes you take). This achievement will unlock in just under 4 full run-throughs of the Oregon journeys.
Living Despite It All (WORK IN PROGRESS)
Journey: Lost Hollow

Goal: Complete Lost Hollow with more than 80 survivors

Prerequisite: N/A

Walkthrough:

Tips: This one is a tough one. Prioritize Meek in your party, even so far as to letting some party members die or walk away so that you save food. You’ll need to play the long game with your survivors, and the waves seem to be randomized with when they come and how many survivors they bring. You’ll have to play the lucky game to keep your numbers up without starving and keeping Meek alive.
Making Her Mark
Goal: Help Little Mary carve her name at Independence Rock

Prerequisite: Attempt to help the family with the broken-down wagon that appears as a random event.

Walkthrough: Your wagon will happen upon another wagon that is broken down, with two adults and a child near the wagon. You have the option to assist them by repairing the wagon or giving them supplies to survive until someone else can help them.

Tips: It does not matter if you are unable to help them (can’t repair wagon, no supplies or money to give), simply having an interaction with them and attempting to repair the wagon will start the quest.
Marcus Whitman
Journey: Prologue, The Nature Trail, The Oregon Trail, Oregon or Bust, Winter Migration, The Chisholm Trail (DLC), The California Trail, Bitter Winter, Ka-Boom, Lost Hollow, Tall Tales

Goal: Complete 20 Route Challenges

Prerequisite: N/A

Walkthrough: Between each of the stopping points, there will be 2 route challenges to complete at random (e.g.- collect meat, restore health, etc)

Tips: Cumulative on all playthroughs. Should be easy to unlock before the end of the first playthrough.
Meek as Moses
Journey: Lost Hollow

Goal: Survive Lost Hollow

Prerequisite: N/A

Walkthrough: There are a multitude of ways to survive until the end of this journey. Basically, all that matters for this achievement is keeping Meek alive until the rescuers arrive. All other party members are expendable. Do whatever it takes to keep Meek in good enough condition to survive random events, snakebites, dysentery, and being forlorn.

Tips: First and foremost, do not get discouraged when playing Lost Hollow. It is the hardest of all the journeys because winning relies half on skill, and half on the RNG working in your favor. Secondly, it appears that Meek almost always will be bitten by a snake on one of the last two or three days before rescuers arrive (It's happened in all of my attempts except one). Save a bottle of medicine until the end.
Midas Touch
Journey: The California Trail

Goal: Collect more than 40 gold nuggets on the California Trail

Prerequisite: N/A

Walkthrough: At the mining site waypoints, having nitroglycerin increases the average number of gold nuggets you receive. Nuggets stack on one tile space in stacks of 10, and can be sold to Assayers at certain stop points.

Tips: Cumulative on all playthroughs. You do not have to have 40 nuggets in your wagon at one time for the achievement to unlock.
Oregon City
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Reach Oregon

Prerequisite: N/A

Walkthrough: Finish an Oregon journey with at least one party member alive.

Tips: The party doesn’t have to be in good condition, they just have to be alive.
Pacific Railroad
Journey: All

Goal: Complete all Journeys

Prerequisite: Unlock all journeys

Tips: N/A
Pawnee Villages (WORK IN PROGRESS)
Journey: Winter Migration

Goal: Complete “Winter Migration”

Prerequisite: Reach Fort Kearny to unlock

Walkthrough:

Tips:
Peperony and Chease
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail, The Chisholm Trail (DLC)

Goal: Leave an epitaph for a character with a custom name

Prerequisite: Complete the “Frail Moment” questline to unlock editable epitaphs.

Walkthrough: Custom name your characters on each playthrough until someone dies (of anything) and then customize their epitaph using the updated options after “Frail Moment” is completed.

Tips: Names cannot be changed after the finalization of the party at your starting point. Of the journeys, Oregon or Bust and The Chisholm Trail (DLC) are rated as the hardest, and provide the most probable chance of death for your party members.
Peppard's Folly
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Successfully fund Samuel Peppard's wind wagon

Prerequisite: N/A

Walkthrough: Along the trail, your party will encounter a random event in which a man falls out of the sky from a "flying machine". Each time you interact with him, choose the encouraging options. You will need to select the route going to Julesburg to speak to the investors there about Peppard, and convince them to fund his project. Keep interacting positively with Peppard and the achievement will unlock when he designs the Wind Wagon.
Performing Sturgery (WORK IN PROGRESS)
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Catch a Lake Sturgeon

Prerequisite: N/A

Walkthrough: Lake Sturgeons appear in the fishing waypoints on the Prairies (Appears to be Leg 1, EXACT SPOTS TO BE DETERMINED)

Tips: The Lake Sturgeon is considered one of the more rare fish types to catch. You will have an increased chance of catching this fish on the "Oregon or Bust" journey than the other two.
Play Right
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Complete Chauncey's play without making a single mistake

Prerequisite: Start the Dragoon Sightings questline

Walkthrough: Agree to be in his play and select any party member to be Spartacus. Select the following options during the play:
i. “…Thrace?”
ii. “…wife?”
iii. “…revenge!”
iv. Fight back
v. “…Thrace anon.”

Tips: For a full list of all Dragoon interactions, including the quest initiation, please click HERE.
Putting the Band Together
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Hear Lewis Southworth perform with a full backing band

Prerequisite: Talk to Lewis Southworth in Fort Laramie to start the quest.

Walkthrough: Lewis will task you with finding a fiddle for him, and finding other musicians to play in his band, and get them to agree to join him in Fort Boise to play. You will need to find the following and successfully get them to join:
  • Guitar and Banjo players (brother and sister pair): You need to take the route that hits Fort Bridger to encounter this pair. Agree with whichever one you want, or neither of them. Tell them about Lewis, and pass a wit check. They will ask you to carry their instruments for them (each is 2 spaces, for a total of 4 spaces). They will take their instruments back right before Fort Hall.
  • Double Bass player: Will appear right before Fort Hall talking to the brother/sister pair. They will take back their instruments, and then Raymond will state he’s giving up being a musician to go live in the mountains. Talk him out of it by telling him how awful mountain life is (the right options) and then pass a composure skill check. He will give you his double bass to carry. It takes up 5 spaces (3 vertical, 1 in the top row, 2 in both the middle and bottom rows). You will need to carry the double bass all the way to Fort Boise.
  • Accordion Player: Will appear before the Snake River Crossing. Invite her to the band, and then compose a good speech to convince her to join (picking Enjoyment, Dreams, and Inspiration has worked for me), and the pass an attitude check. If you pass the check, Cleo will give you the accordion to carry in your wagon. The accordion takes up 4 spaces (2x2, the same shape as meat or foodstuffs). You will need to carry the accordion to Fort Boise.
  • Buy a Fiddle: You need to take the southern route after the Three Islands to find the fiddle seller on the last stop (second Snake River Crossing). There are a few options here on how to acquire the fiddle, up to and including taking an IOU if you have no money at all. Lowering the price involves wit checks, so either a high wit or a “Charming” personality party member will pass with ease. You will need to cross the last Snake River Crossing with the fiddle and arrive at Fort Boise.

Tips: You will not be able to acquire all 3 achievements for Lewis' quests during the same run-through, as one requires you to get an IOU (meaning Lewis will pay the IOU) for the fiddle, or you pay for the fiddle and not allowing Lewis to pay you back. Either of those can be completed in tandem with this achievement, but not both.
Rendezvous (WORK IN PROGRESS)
Journey: Rendezvous

Goal: Complete "Rendezvous"

Prerequisite: Complete the “Pushed West” journey to unlock.

Walkthrough:

Tips:
Robert Newell
Journey: All except The Tranquil Trail, Lost Hollow, Rendezvous, White Water, A Fur Trade

Goal: Complete 1,000 events

Prerequisite: N/A

Tips: Every random event that occurs on the trail counts as 1 event. If you decline to participate in the event (bypassing the dog, not inspecting/picking the berries, etc), it will not count towards this total.
Rufus Porter
Journey: N/A

Goal: Complete 15 Contracts

Prerequisite: N/A

Tips: This will take 15 weeks to complete if you are able to complete each contract every week without missing or failing.
Sager Orphans
Journey: N/A

Goal: Collect 25 Gallery Items

Prerequisite: N/A

Walkthrough: Complete the weekly contract and community railroad to earn 4 tokens and 3 tokens respectively.

Tips: Use those tokens to purchase artwork for 1 token each. That's the quickest way to reach 25. If you pick the correct railroad and complete the contract each week, it will take 4 weeks to reach 25 tokens.
Sail On!
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail, The Chisholm Trail (DLC)

Goal: Travel 500 miles using a wind wagon

Prerequisite: Complete the quest “Peppard’s Folly” on one of the Oregon journeys to unlock the wind wagon.

Tips: The wind wagon does not have a ton of available space. Use the available space wisely.
Shooting Hoops
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Witness a hoop snake

Prerequisite: DLC required to unlock “Story” campsite waypoints.

Walkthrough: Stay at a “Story” campsite waypoint for a chance to unlock this random event.
Sing-along
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail, The Chisholm Trail (DLC)

Goal: Have a musician play for the rest of the party at a campsite

Prerequisite: Unlock the musician class by completing Lewis Southworth’s quest and bringing all 5 musicians together to play (see “Putting the Band Together” achievement section above).

Walkthrough: Which a musician in your party, stop at any "Campsite" waypoint and select "Play Music" from the options.

Tips: Make sure to keep the musician’s instrument in your wagon, or they will not be able to play.
Skillful
Journey: The Oregon Trail

Goal: Discover all of your party's skills in "The Oregon Trail"

Prerequisite: N/A

Walkthrough: Skillsets can be unlocked by increasing/decreasing the skill, or attempting to use the skill. Skills can also be discovered by stopping at any campsite (except the “Stories” camp from the DLC), and selecting “Tell Stories”. This will reveal 4 random skills from the party that are currently undiscovered. Skills are as follows:
  • Attitude- Can be discovered by fishing, some random events
  • Carpentry- Can be discovered attempting to repair wagon, or in random events that involve repairing others’ wagons.
  • Composure- Can be discovered by using a Hymn Book to increase composure by 1, or 2 for Missionaries/”Religious” personality party members.
  • Loyalty- Can be discovered during random events
  • Medical- Can be discovered through attempting to heal other party members during random events
  • Shooting- Can be discovered through hunting, or random events that involve shooting challenges (Gunslinger, velvet antler deer, prairie dog, etc)
  • Wayfinding- Can be discovered through attempting to pick berries, random events that involve directing people, assisting the railroad workers at stopping locations with coal finding, or by using the Guidebook to increase the skill.
  • Wit- Can be discovered by haggling, Obadiah's Dragoon challenge, He-Dow's conversation with the Mormons.

Tips: You will need to keep all party members alive until you know their full skillset.
Sky High
Journey: The California Trail

Goal: Have a nitroglycerin explosion cause the death of a character

Prerequisite: N/A

Walkthrough: You will need to have a party member’s health reach 0 with a nitro explosion, or while having burns from a previous nitro explosion. The easiest way to do this is to get their health to 1, have them with low composure, and have them place the nitro at the mining sites.

Tips: The lower their composure, the more likely the nitro will accidentally discharge, or fail to ignite and require them to try again.
Slippery as an Eel
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Catch a Pacific Lamprey


Prerequisite: N/A

Walkthrough: Pacific Lamprey appear in the fishing waypoints on the Snake River Valley (leg 4) and the Mountains (first two parts of Leg 5).

Tips: The Pacific Lamprey is considered one of the more uncommon fish types to catch. You will have an increased chance of catching this fish on the "Oregon or Bust" journey than the other two.
Smithereens
Journey: The California Trail

Goal: Have the wagon break down as a result of a nitro explosion

Prerequisite: N/A

Tips: Do not have a Prospector in your party, pack the nitro close together, and do not repair your wagon. A Prospector lowers the chance of the nitro accidentally exploding. Packing the nitro closer together increases the chance of an explosion. If you do not repair your wagon, each turn is a higher chance of a square holding nitro being damaged, and thus exploding.
Sob Story
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Witness a squonk

Prerequisite: DLC required to unlock “Story” campsite waypoints

Walkthrough: Stay at a “Story” campsite waypoint for a chance to unlock this random event.
Spice of Life
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail

Goal: Have a Cook character make a perfect dish

Prerequisite: DLC required to unlock “The Chisholm Trail”. Complete “The Chisholm Trail” to unlock the Cook class.

Walkthrough: Bring a Cook with you on any trail besides “The Chisholm Trail” and have them cook with their spice set at the “Cooking” campsite.
Take Your Chances
Journey: Lost Hollow

Goal: Successfully complete 5 salvage events in a row

Prerequisite: N/A

Walkthrough: Each day you get a chance to send out survivors to salvage supplies. The more survivors you send out, the better chance of successfully completing a salvage event, but the higher the likelihood that some survivors (or all) may not survive.

Tips: This journey is an RNG nightmare. It may take a few attempts in order to unlock this achievement.
Taking Credit
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail,

Goal: Complete your Individual Goal for the week

Prerequisite: N/A

Walkthrough: Pick your team for the railroad in weekly events, and then it will give you a goal to complete. Complete the goal prior to the deadline (subject to change based on your timezone).

Tips: Coal, nitroglycerin donation, toolbox donation, and bonds are located at stopping points. Assisting the workers happens along the trail.
Television
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail, The Chisholm Trail (DLC)

Goal: Obtain a score of 15,000

Prerequisite: N/A

Tips: Finish the game with your wagon in the best possible condition, all 4 (or as many as possible) party members in the best possible health, and money in the wagon to receive a higher score. The California Trail has an additional category for remaining gold nuggets, and The Chisholm Trail (DLC) has an additional category for the condition of the cattle in the cattle drive.
Texas Fever
Journey: The Chisholm Trail (DLC)

Goal: Arrive at Abilene in Kansas

Prerequisite: DLC required to unlock “The Chisholm Trail”

Walkthrough: N/A
That’s a Paddlin’
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Catch a Paddlefish

Prerequisite: N/A

Walkthrough: Paddlefish appear in the fishing waypoints on the Prairies (Leg 1 before Fort Kearny, in Rivers)

Tips: The Paddlefish is considered one of the more uncommon fish types to catch. You will have an increased chance of catching this fish on the "Oregon or Bust" journey than the other two.
The Last Spike
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail

Goal: Help your chosen railroad company claim victory

Prerequisite: N/A

Walkthrough: In the Community Events, select one of the railroads and complete your weekly individual goal. If your railroad wins (completes more than 50% of the railroad), this achievement will unlock.

Tips: If you do not complete your weekly goal, it will not count as a win for this achievement, nor for the internal game achievements (unlocking the specialized wagon or awarding the gallery tokens).
The Oregon Trail (2009)
Journey: All

Goal: Complete 75% of all Journal Challenges

Prerequisite: N/A

Walkthrough: The journal contains 100 challenges to complete along your journey, including everything from spotting animals to having characters die in certain ways.

Tips: Set your accessibility settings to auto-click on the animals so that you can focus on playing the game (this is highly recommended if you are playing on Steam Deck and/or using a controller).
The Oregon Trail (2021)
Journey: All

Goal: Complete 100% of Journal Achievements

Prerequisite: DLC required to complete all 100 journal challenges

Walkthrough: The journal contains 100 challenges to complete along your journey, including everything from spotting animals to having characters die in certain ways.

Tips: Set your accessibility settings to auto-click on the animals so that you can focus on playing the game (this is highly recommended if you are playing on Steam Deck and/or using a controller).
The Peoria Party
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust

Goal: Reunite the Dragoons

Prerequisite: N/A

Walkthrough: Meet all 10 of the Dragoons and convince the last 9 to return to the team by solving whatever issue they are having or challenge they are presenting.

Tips: Please click HERE to view the guide on how to convince each Dragoon to return.
The Real Work Begins
Journey: The California Trail

Goal: Have a Prospector character make it to California

Prerequisite: Complete “The California Trail” to unlock the Prospector class.

Walkthrough: N/A
Thief in the Night
Journey: The Nature Trail, The Oregon Trail, Oregon or Bust, The California Trail, The Chisholm Trail (DLC)

Goal: Have an in-going or outgoing theft of supplies

Prerequisite: N/A

Walkthrough: This achievement can be triggered as a random event where the party stops for the night. Decline to have someone stand watch for the night, and there's a chance that a bear will ransack your wagon. Otherwise, stay at the "Rest" campsites, and there is a chance that a thief will steal some of your supplies.

Tips: These are more likely to occur on The Oregon Trail than The Nature Trail, and Oregon or Bust more than The Oregon Trail.
Trail Food
Journey: Prologue, The Nature Trail, The Oregon Trail, Oregon or Bust, Winter Migration, The Chisholm Trail (DLC), The California Trail, Bitter Winter, Ka-Boom, Lost Hollow, Tall Tales

Goal: Consume 1,000 pounds of food

Prerequisite: N/A

Walkthrough: This achievement will progress without any action needing to be taken by the player. Simply keep playing and this will unlock.

Tips: This is cumulative on all playthroughs. A party of 4 on “Filling” rations will consume 1,000lbs of food in 63 days, 1,000lbs in 84 days on “Meager” rations, and 1,000lbs in 125 days on “Bare Bones” rations. This should be easy to unlock before the end of the first playthrough if all of your characters stay alive.
Trail Mortality
Journey: Oregon or Bust

Goal: Complete “Oregon or Bust”

Prerequisite: Complete “The Oregon Trail” journey to unlock.

Tips: This is just like “Nature Trail” and “The Oregon Trail” journeys, but way harder. This means the chance of bad things happening goes up, and luck goes down. This journey is fantastic for getting the achievements that require bad things to happen (party members dying, failing a river crossing, etc).
Trail Wildlife
Journey: The Nature Trail

Goal: Complete "The Nature Trail"

Prerequisite: N/A

Walkthrough: At least one party member must reach Oregon City alive.

Tips: This is the easiest version of the legacy Oregon Trail route. Recommended to be used for first playthrough or playthroughs that are for animal sighting achievements.
Wagons
Journey: Multiple

Goal: Complete a Journey with 3 different wagons

Prerequisite: Unlock additional journeys.

Walkthrough: On 3 different journeys (or journey playthroughs), make sure to finish them with 3 different styles of wagons. Styles of wagons are as follows:
  • Small Wagon
  • Murphy Wagon
  • Conestoga Wagon
  • Wind Wagon
  • Horse
Winter (WORK IN PROGRESS)
Journey: Bitter Winter

Goal: Complete “Bitter Winter”

Prerequisite: Complete the “Winter Migration” journey to unlock.

Walkthrough:

Tips: Keep an eye on your party members' health. Not all the footprint waypoints will lead to discovering party members and may result in unnecessary time lost.
You Can't Eat It
Journey: The California Trail

Goal: Trade 5 or more gold nuggets for supplies

Prerequisite: N/A

Walkthrough: While at a stopping point (cities, rivers, etc), trade 5 of your gold nuggets for other supplies.

Tips: This is cumulative on all playthroughs.
You have died of dysentery
Journey: All journeys except The Tranquil Trail, Rendezvous, White Water, and A Fur Trade

Goal: Lose a character to dysentery

Prerequisite: N/A

Walkthrough: Once the party member has dysentery, allow their health to hit 0 and they will die.

Tips: When a party member’s hygiene hits 0, there’s a higher chance of them contracting dysentery. Random events will also offer the chance for a party member to drink from a pool of water, which also gives a chance of the party member contracting dysentery.
1 Comments
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SoulSteppe 27 Jun @ 4:33am 
Do you have a 100% save file?