Oregon Trail Side Quests (2024)

The Star-Crossed Lovers Quest

A Chance Encounter (The Star-Crossed Lovers Quest Part 1)

A man called Douglas seeks a girl he met, Ava. He wants her to meet him at Fort Laramie.

  • Talk to Douglas in Independence

    • Ask who Ava is

He describes her and asks you to tell her he’ll be at Fort Laramie if you meet her

  • Agree to assist

  • Decline

  • Say no

A Fated Meeting (The Star-Crossed Lovers Quest Part 2)

The party meets Ava, Douglas’ love. She declares her love for him but her father disapproves of the marriage. She is thinking of running away to find Douglas.

  • Talk to Ava at Alcove Spring. She wants to leave her dad’s team.

    • Tell her about Douglas

      • Offer supplies (-150 food)

      • Offer supplies (-$50)

      • Leave

      • Discourage her

    • Offer supplies (-150 food)

    • Offer money (-$50)

    • Discourage her

A Promise Broken (The Star-Crossed Lovers Quest Part 3)

The team meets Harold, Ava’s father. He is looking for Ava and you have the chance to keep her location a secret or tell him where she is going. He will be at Fort Laramie for 4 days.

  • Keep an eye out for Ava

Harold gives the team +25 floor as an incentive to look for Ava

  • Tell him about Ava

  • Decline

A Promise Made (The Star-Crossed Lovers Quest Part 4)

The team meets Ava and Douglas at Independence Rock. They’re on their way to Fort Bridger to be married and invite the team to witness it.

  • Accept Invitation

Ava is happy that the team will attend

  • Tell them about the father

Ava is alarmed and leaves with Douglas immediately. This will end the Quest.

  • Can’t Make It

A Promise Fulfilled (The Star-Crossed Lovers Quest Part 5)

The team meet up with Ava and Douglas at Fort Bridger and witness their marriage.

  • +200 Flour

*QUEST COMPLETE*

Peppard’s Folly Quest

Twisting in the Wind (Peppard’s Folly Part 1)

While walking towards the Kansas River Crossing, a man and his wagon fall out of the sky.

  • Assist Him

Man gets up and introduces himself.

  • Marvel at his idea

  • Dismiss his idea

  • Leave

Peppard’s Second Wind (Peppard’s Folly Part 2)

The team comes across Samuel Peppard on the way to Alcove Spring. He is working on a new idea.

  • Encourage Him

Samuel is wanting to make a wagon with a sail. He believes there are investors in Julesburg. He would like you to talk to them on his behalf.

  • Discourage Him

Something in the Wind (Peppard’s Folly Part 3)

The team meets William Thomas at Fort Kearney, who has made his own Wind Sail Wagon.

  • Mention the investors

Tell William about the investors in Julesburg. He asks the team to talk to the investors on his behalf.

  • Mention Samuel Peppard

Tell William about Samuel Peppard’s wagon

  • Give Him Your Support

  • Discourage Him

Get Wind of This (Peppard’s Folly Part 4)

The team arrives in Julesburg and speaks to the investors.

  • Mention Samuel Peppard - asked what you should talk about

    • The flying machine

    • The wind wagon

Both bank people are very interested in Peppard’s wind wagon and thank the team for mentioning it.

  • Peppard’s wealth (lie)

  • Mention William Thomas

  • Mention William Thomas

    • William Thomas’ sales pitch

    • The general percentage

    • Mention Samuel Peppard

  • Leave

The Way the Wind Blows (Peppard’s Folly Part 5)

The team finds either Samuel Peppard or William Thomas and the Bank investors standing together.

  • Let’s See It!

  • Ask about the future

*QUEST COMPLETE*

The Wind Wagon is now available to buy on future trips.

Lost in Translation Quest

Lost in Translation (Part 1)

The party comes across Black Beaver and his family, who are traveling to a treaty signing. His sister, Annie Halfmoon, apologizes for him.

  • Ask if everything is alright

Annie Halfmoon explains their father, Joseph Halfmoon, is very sick which requires frequent breaks.

  • Offer assistance

    • Offer 1 medicine

      • Ask more about the treaty

Black Beaver explains the treaty in greater detail

  • Leave

  • Offer an examination

  • Leave

  • Ask about their destination

Annie Halfmoon explains about the treaty

  • Leave

  • Push on

As the Crow Flies (Lost in Translation Part 2)

The party meets Bíawacheeitchish. She is also traveling to the treating signing and is willing to trade some of the supplies she has.

  • Trade for 5 Blankets

  • Trade for 150 Meat

  • Trade for 3 Fish Traps

  • Trade for 6 Pelts

  • Leave

Conflict Resolution (Lost in Translation Part 3)

The party comes upon a US soldier and a group of Lakota who are in disagreement over payment for entering Lakota land. Black Beaver is there with his sister and father. He asks if the party can help.

  • Speak with Mato Oyuhi

Mato Oyuhi has been chosen to represent his party of Lakota. He explains that to enter Lakota land, a toll is required. He is also not confident that the upcoming treaty will help relations between the Lakota and the US government.

  • Speak with US Soldier

A man called Thomas Fitzpatrick interrupts, saying he is the man who organized the treaty. He explains the soldiers were assigned to protect him. The US soldier steps in and explains that he has not been authorized to pay a toll to the Lakota. He also believes he shouldn’t have to. He says a toll will limit access to the treaty and that the treaty will compensate for the toll.

  • Side with US Soldier

  • Side with Mato Oyuhi

    • Choose the Character with the highest Wit level to convince the US Soldier

      • Speak with US Soldier again

      • Speak with Mato Oyuhi again

Horse Creek Camp (Lost in Translation Part 4)

The party comes to the treaty signing not far from Fort Laramie.

  • Talk to Bíawacheeitchish

  • Talk to Thomas Fitzpatrick

  • Talk to Mato Oyuhi

  • Talk to Black Beaver

  • Proceed to signing

    • Talk about the signing

    • Leave

*QUEST COMPLETE*

A Frail Monument Quest

Precious Little (A Frail Monument Part 1)

The team comes across a disheveled couple and little girl. Their wagon is broken and they need help.

  • Ask what happened.

The wife Jane explains what happened.

  • Offer to repair their wagon

Pick the person with the highest Carpenter level or the Carpenter to try to repair the wagon. The axle is broken. It can be replaced or an attempt to repair can be done.

  • Try to Repair. Team member chosen loses -1 Stamina.

  • Replace with spare axle (if you have one on your wagon).

  • Offer supplies

    • Give them 50/100 food

  • Push On

Gifted Child (A Frail Monument Part 2)

The team finds the family they helped on the trail. Thanks to your help (either fixing their wagon or giving them food) they have made it to Fort Kearney safely. They give the team a gift of +1 harmonica. From this point on, you will see the little girl at other stops along the trail and you have the choice to engage the family to continue the quest and gain the achievements, or ignore them. It will not affect your journey either way.

Rag Doll (A Frail Monument Part 3)

The team meets the family with little Mary on the trail. She is excited to see them and tells them her birthday is coming up soon. The parents ask the team to help them make a rag doll for her birthday present. Any team member can be chosen. Afterwards the team continues on.

Forever and Ever (A Frail Monument Part 4)

Little Mary and her parents are at Independence Rock, and her mom asks for someone to find her. Choose the team member with the highest stamina. The character finds Little Mary a few hours later, where she wants to carve her name on the rock.

  • Help her carve name

The character helps Mary carve her name then takes her back to her mom.

  • Take her down off rock

Child’s Play (A Frail Monument Part 5)

The team meets Little Mary and her parents at Soda Springs, where Mary is playing in the water. Her mom asks if someone can keep an eye on her.

  • Talk to Little Mary

    • Yes

      • Yes

      • No

    • No

  • Leave her alone

Worried Sick (A Frail Monument part 6)

The team meets with Little Mary and her parents on the trail. Her mother is concerned because Mary is sick. She says Mary is very fond of the team since she met them.

  • Speak to Little Mary

    • Her New Home

    • Toys

    • Dresses

    • Her Birthday

After asking her a couple of questions, she is caught in a fit of coughing so the questions stop.

  • Offer Medicine - 1 Medicine

  • Leave

  • Offer Medicine - 1 Medicine

Frail Monument (A Frail Monument Part 7)

The team comes across the gravestone with wild flowers…and a little doll.

  • -2 Party Morale

*QUEST COMPLETE*

The Peoria Party Quest

The Peoria Party

The team comes upon a group of men leaving their leader. He explains that they hoped to blaze a trail to Oregon and called themselves the Oregon Dragoons. But the party fell apart and the leader asks the team members to convince his party to meet him further on the trail.

  • Who Are You?

The man explains who he is and who the group is.

  • Agree to Help

The team agrees to help convince the party to reunite. This will open up new Trail Stops you can choose to travel to where each man has a different mini quest for the team to do. If successful, the team earns a Dragoon Medallion, which can be kept or used for trade along the trail. Collect all medallions to earn the Oregon or Bust Wagon. Make sure to have 1 pair of clothes, medicine, and money available to finish some of the quests.

  • Refuse

The team refuses to help the man. He tries to guilt the team into helping. You can change your mind or continue to refuse and the quest does not begin.

Dragoon Sighting (The Riddler)

The party finds Obadiah Oakley from the Oregon Dragoons. He hates traveling alone and wants to play a little game. He will ask the party three riddles and they must get them correct to please him. The riddles asked will be different each play through.

  • Accept

There are several riddles that could be asked

  • Riddle: Slayer of regrets, old and new, sought by many, found by few. What am I?

    • Answer: Redemption

  • Riddle: I speak without a mouth and hear without ears. I have no body, but come alive with wind. What am I?

    • Answer: An echo

  • Riddle: What breaks and never falls, and what falls and never breaks?

    • Answer: Day and night

  • Push on

Dragoon Sighting (The Rider)

The party finds Robert Moore, who demands a ride on the wagon. His irregular shape takes up space in the wagon for a short distance before he jumps out and walks away. To leave him behind, discard him like items from the wagon. If taken, he will give +1 Dragoon Medallion.

Dragoon Sighting (The Thespian)

The party comes across Chauncey Wood, who is set on putting on a performance of Robert Bird’s ‘The Gladiator’. His lead actor has left and he needs a Character to play the role of Spartacus. If the play is done properly, he will give the party +1 Dragoon Medallion plus $50

  • Choose any Character

    • Begin the show

During the show you must choose the correct response to keep the play going and the crowd happy.

  • Correct Responses in order:

    • …Thrace?

    • …wife?

    • …revenge!

    • Fight back

    • …Thrace anon

  • Review script

Lines, in yellow, will be needed to choose the correct choice during the show. The lines are:

  • “Is it a thousand leagues away to Thrace?”

  • “Great degradation. No matter: I am sworn to be a caitiff. Where have you placed my wife? It was conditioned, you should not part us.”

  • “Ho, slaves, arise! It is your hour to kill! Kill and spare not - for wrath and liberty! Freedom for bondmen - freedom and revenge!”

  • Next is an action that must be chosen, which is to fight the other actor.

  • “Well - never heed the tempest - there are green valleys in our mountains yet. Set forth the sails. We’ll be in Thrace anon.”

  • Decline

Dragoon Sighting (The Investigator)

The party finds Joseph Holman, who is trying to help investigate a murder in a wagon train. The longest Dragoon event. +1 Dragoon Medallion

  • Investigate

    • Overview

    • Suspect dossiers

      • Quill Peabody (right handed and wears large boots, closest match to handwriting)

      • Gareth Fairfield (left handed with average foot size, no match to handwriting)

      • Kellogg Hardin (ambidextrous and average-sized boots, handwriting sample bad)

      • Gurney Goldman (right-handed and small footed, neat writing that doesn’t quite match)

      • Marshall Brennan (right handed with small feet, handwriting is terrible)

      • Back

    • Interview suspects

      • Quill Peabody

        • Alibi?

        • Victim relationship

        • Examine

        • Back

      • Gareth Fairfield

        • Alibi?

        • Victim relationship

        • Examine

        • Back

      • Kellogg Hardin

        • Alibi?

        • Victim relationship

        • Examine

        • Back

      • Gurney Goldman

        • Alibi?

        • Victim relationship

        • Examine

        • Back

      • Marshall Brennan

        • Alibi?

        • Victim relationship

        • Examine

        • Hit Kellogg?

        • Back

    • Investigate evidence

      • Crime scene

      • Ruined letter

      • Murder weapon

      • Back

    • Make accusation

      • Quill Peabody

      • Gareth Fairfield

      • Kellogg Hardin

      • Gurney Goldman

      • Marshall Brennan

    • Recap

  • Decline

(Spoiler: It’s Marshall Brennan. Here are the answers to the questions for why he’s guilty:)

  • Continue

    • Not right-handed

      • Bruise

        • Wasn’t muddy

          • Wasn’t raining

            • He was interrupted

              • Thefts’ mastermind

Dragoon Sighting (The Nudist)

The party sees John Pritchel standing in a bush with nothing but his long johns on. +1 Dragoon Medallion.

  • Give 1 Clothes

  • Push on

Dragoon Sighting (The Sleeper)

The party sees a Dragoon member sound asleep. They can try to wake him up. (It will take 3 tries every time before he wakes up. Don’t waste anything.)

  • Fire a gun

  • Give him coffee

  • Wait

  • 6 hours

  • Yell at him

  • Kick him

  • Push on

Dragoon Sighting (The Answer Man)

The party comes upon a man at a table called Amos Cook, who’s been hired to give guidance to travelers. He states that if the party handles the last of the travelers, he’ll return to the company.

  • Choose a Character to answer questions.

    • The first traveler will never be happy with whatever you say, so don’t worry about it.

    • The second traveler

      • Greetings

        • Interrupt

        • Wait

          • Soda Springs

      • Say nothing

    • The third traveler

      • Greetings

        • 1848 (look at the top of the screen)

      • Say nothing

Dragoon Sighting (The Fighter)

The party finds Ralph L. Kilbourne surrounded by angry men, asking for help. He owes the men $50. The Creditor tells the party to move along.

  • Intervene

    • -Pay $50 (creditor says that with interest, there’s $75 more owed)

      • Pay $75

      • Refuse

        • Choose the Character with the highest Attitude level to argue with the Creditor

    • Argue

    • Push on

  • Push on

Dragoon Sighting (The Shooter)

The party hears a gunshot and finds a Dragoon on the ground in pain, badly injured.

  • Give him Medicine

  • Heal without medicine

    • Choose the Character with the highest Medical level or the Doctor

  • Push on

The Peoria Party (Part 2)

The team sees the Dragoons gathered together and speak to the leader, who thanks them for finding some or all of the Dragoons. He rewards the team with money.

*QUEST COMPLETE*

The Ballad of Lewis Southworth Quest

On A Mission (The Ballad of Lewis Southworth Part 1)

At Fort Laramie, the team can talk to Lewis Southworth, a musician heading west who is trying to put together a band. He asks them to find a fiddle for him.

  • Offer to Help

    • Promise to buy a Fiddle

Lewis says he can earn money back to pay the team for the fiddle if they buy one. He also tells the team of a brother and sister who play guitar and banjo that could join him. They were last seen heading to Fort Bridger.

  • Ask About Fiddle

Lewis explains there are always people trying to sell instruments on the trail and says to ask.

  • Ask about fiddle value

Lewis says that a good fiddle is no more than $30. More than that is a rip off.

  • Agree to his plan

Lewis tells the team he will meet them at Fort Boise, much further along the trail, to give them time.

  • Turn him down

  • Leave

Sibling Revelry (The Ballad of Lewis Southworth Part 2)

The team sees a duo playing the guitar and the banjo on the trail. It is the brother and sister that Lewis Southworth was looking for. They are arguing about why they don’t have fans.

  • Support brother

  • Support sister

    • your inspiration!

    • your audience!

      • The picturesque scenery

      • A waiting crowd

      • Mention Lewis Southworth

        • Choose the character with the highest level of Wit or with the Charming trait to convince the siblings to meet Lewis Southworth.

          • They ask the team to carry their instruments for a way as they go to join Lewis Southworth

  • Support neither

  • Leave

Measure of a Mountain (The Ballad of Lewis Southworth Part 3)

The team sees the brother and sister musicians on the trail with a man playing a bass. They ask for their instruments back while the team tries to convince the bass player to join Lewis Southworth’s band. He wants to sell his bass and go to the mountains.

  • Invite to the band

He doesn’t want to join the band.

  • Compliment his playing

    • Express desire for bass

    • Mention the cold

      • Enthuse about crowds

      • Discuss clothes making

      • Choose the character with the highest Composure level to convince the bass player not to go into the mountains. +1 clothes. He asks the team to carry his bass for him in the wagon.

  • discuss mountain life

  • Offer him $5

  • Ask about fiddle

The bass player says he heard of a man selling one on the Snake Rivers

  • Leave

(Team will have to carry double bass if he agrees. Similar in shape to Flour.)

Downbeat (The Ballad of Lewis Southworth Part 4)

The team finds a young woman, Cleo, playing an accordian on the trail. They think she will work in Lewis Southworth’s band. Her father doesn’t want her to keep playing and she is about to sell her instrument.

  • Invite to the Band

    • The team has to think of a way to convince Cleo to join the band. First they have to choose an opening topic.

      • Parents

      • Enjoyment

      • Accordions

        • Next they need to choose the middle part

          • Musical notes

          • Stress Relief

          • Dreams

            • Now choose the ending

              • Confidence

              • Inspiration

              • Songs

                • Next choose the team member with the highest level of Attitude

                • If successful, she asks the team to carry her accordion for her so her parents don’t see it.

  • Ask about Fiddle

She informs the team that there is salesman a little further down the Snake River who has one

  • Leave

(If she agrees, the party will need to carry her accordion in the wagon, a 2x2 square)

Top Billing (The Ballad of Lewis Southworth Part 5)

The team comes to Lewis Southworth at his stage with the rest of the band members, all of them ready to perform. All instruments are removed from the wagon. The band performs and Lewis speaks to the team afterwards. There will be different options based on how the fiddle was paid for. If you have an IOU with the Salesman, Lewis will take it to pay him.

*QUEST COMPLETE*

Musician class is unlocked

Hold Your Piece Quest

The Gunslinger (Hold Your Piece Part 1)

A man approaches the party, stating he needs to hone his shooting skills and asking if they fancy a wager. He’ll spot the bullets

  • Accept the challenge

    • Choose the Character with the highest Shooting level

      • Bet $10

      • Bet $20

      • Bet $50

        • Find and select the button that says Hit three times

  • Politely decline

A Sharp Eye (Hold Your Piece Part 2)

The party once again meets the Gunslinger, who once again wants to wager with them on who shoots the best. This time the party has to wait until his friend says “Go!” while also being distracted by other sounds.

  • Accept the challenge

    • Bet $10

    • Bet $20

    • Bet $50

      • Ready

        • Choose either the Fire! button or the Wait button when George specifically says “Go!”

  • Politely decline

A Tricky Shot (Hold Your Piece Part 3)

The party meets the Gunslinger again. He offers a rematch. Both take three shots, each target further away than the last. If the target is shot, the bet can be cashed in right away or bet again to take the next shot. If you miss a shot, you’re done. The higher the Character’s Shooting level, the higher the chance of hitting all three targets.

  • Accept the challenge

    • Bet $10

    • Bet $20

    • Bet $50

      • Asks name

  • Politely decline

Oregon Trail Side Quests (2024)
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