- 10IndependenceReach Independence
- 10Thief in the NightHave some supplies stolen
- 10Columbia RiverComplete "White Water" with at least 10,000 points
- 10You have died of dysenteryLose a character to dysentery
- 10SkillfulDiscover all of your party's skills in a single run in "The Oregon Trail"
- 10Robert NewellComplete 1,000 events
- 10BisonCollect 1,000 animals
- 10The Oregon Trail (2009)Complete 75% of Journal Achievements
- 10WinterComplete "Bitter Winter"
- 10RendezvousComplete "Rendezvous"
- 10Pawnee VillagesComplete "Winter Migration"
- 10Trail WildlifeComplete "The Nature Trail"
- 10Trail MortalityComplete "Oregon or Bust"
- 10AntiquesDeliver an antique to Oregon
- 10Oregon CityReach Oregon
- 10WagonsComplete Journeys with 3 different wagon types
- 10Big Blue RiverCross the Big Blue River without incident
- 10Trail FoodConsume 1,000 pounds of food
- 10Fort LaramieDiscover Fort Laramie
- 10Fort HallDiscover Fort Hall
- 10Fort BoiseDiscover Fort Boise
- 10TelevisionObtain a score of 15,000 or more
- 15Lewis and ClarkTravel 8,000 total miles
- 15John Jacob AstorSpend a total of $20,000
- 15Pacific RailroadComplete 100% of Journeys
- 15The Oregon Trail (2021)Complete 100% of Journal Achievements
- 15Independence RockReach Independence Rock on or before July 4
- 15Marcus WhitmanComplete 20 Route Challenges
- 15James BeckwourthWin against Beckwourth in "Tall Tales"
- 15Putting the Band TogetherHear Lewis Southworth perform with a full backing band
- 15Sing-alongHave a musician play for the rest of the party at a campsite
- 15A Good CauseMake sure Lewis Southworth keeps all the money from his performance
- 15Play RightComplete Chauncey's play without making a single mistake
- 15Going for GoldHave all 10 Dragoon Medallions at once
- 15The Peoria PartyReunite the Dragoons
- 15Douse the FireTalk the Gunslinger out of his quest for vengeance
- 15Fettuccine WesternWin all 5 of the Gunslinger's challenges
- 15A Fistful of GreenbacksWin $100 or more in total from the Gunslinger's challenges
- 15Frail MonumentMake sure Little Mary gets a doll for her birthday
- 15Making Her MarkHelp Little Mary carve her name into Independence Rock
- 15Peppard's FollySuccessfully fund Samuel Peppard's wind wagon
- 15Sail On!Travel 500 miles using a wind wagon
- 15Flying Like a BirdHave a unique encounter while traveling with a wind wagon
- 15Meek as MosesSurvive Lost Hollow
- 15Take Your ChancesSuccessfully complete 5 salvage events in a row
- 15Living Despite It AllComplete Lost Hollow with more than 80 survivors
- 15Dare Go HollowComplete Lost Hollow in fewer than 15 days
- 15All Your Fish in a RoeCatch every trophy fish
- 15Give a Man a FishTrade away a total of 500 pounds of fish
- 15Chasing RainbowsCatch a Yellowfin Cutthroat Trout
- 15That's a Paddlin'Catch a Paddlefish
- 15Performing SturgeryCatch a Lake Sturgeon
- 15Slippery as an EelCatch a Pacific Lamprey
- 15Midas TouchCollect more than 40 gold nuggets on the California Trail
- 15Count Your FingersUse Nitro at least 12 times on the California Trail
- 15Gold in the VeinsHave the party activate Gold Fever
- 15You Can't Eat ItTrade 5 or more gold nuggets for supplies
- 15Gold-FashionedTrade supplies for gold nuggets 3 times on the trail
- 15Golden SunsetArrive at Sutters Mill in California
- 15Cashing InSell at least 25 gold nuggets to an Assayer
- 15Fool Me TwiceGet swindled with Fool's Gold twice
- 15SmithereensHave the wagon break down as a result of a nitro explosion
- 15Sky HighHave a party member killed by a nitro explosion
- 15Cooling DownUse medicine to heal a Burned character completely
- 15The Real Work BeginsHave a Prospector character make it to California
- 15Follow the StarsListen to John Evans's story
- 15In the Pursuit of KnowledgeMake a donation to the museum
- 15Fact or FictionBecome lost while searching for the meteorite
- 15Rufus PorterComplete 15 Contracts
- 15Sager OrphansCollect 25 Gallery items
- 15Abigail Scott DuniwayCollect 50 Gallery items
- 15Taking CreditComplete your Individual Goal for the week
- 15The Last SpikeHelp your chosen railroad company claim victory
- 15Peperony and CheaseLeave an epitaph for a character with a custom name
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DLCCowboys and Critters
- 10Sob StoryWitness a squonk
- 10Shooting HoopsWitness a hoop snake
- 10Fish StoryWitness a Flambeau ambler
- 10Back And ForthWitness a filla-ma-loo bird
- 10Texas FeverArrive at Abilene in Kansas
- 10Bet the RanchReach Abilene with excellent cattle condition
- 10Behind the NameMeet Jesse Chisholm
- 10In Good TasteCook a cowboy's favorite dish
- 10Spice of LifeHave a Cook character make a perfect dish
Gameloft
The Oregon Trail
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