The Oregon Trail - All Dragoon Sighting Encounters Guide (2024)

This guide will be showing you all the Dragoon Sighting encounters in The Oregon Trail.

All Dragoon Encounters

The roster presented below is organized alphabetically based on the quest-giver. Nevertheless, in the game, the appearance order of the Dragoons is entirely random. These Dragoon encounters occur in the stretch between Fort Kearny and Fort Boise, corresponding to legs 2 through 4 of the journey. It’s important to note that it’s not feasible to interact with every Dragoon waypoint that spawns. However, by following the path with the highest number of spawns, you can collect all 10 medallions required for the quest. Should you choose to skip any of the Dragoon waypoints, you won’t be able to obtain all 10 medallions as they are essential for completion.

On a fascinating note, it’s worth mentioning that all these characters are based on real historical figures who existed. The Peoria Party, a group of pioneers, split into multiple factions, each embarking on their own distinct journeys. Interestingly, they never reunited during their travels.

Thomas Farnham (Quest Giver)

Problem: All the Dragoons left and Thomas needs them back.

Solution: Agree to help to start the questline.

Tips: N/A

Amos Cook (Help Desk)

Problem: Amos is running essentially a help desk, and needs a break.

Solution: Answer questions for him. There will be three passing parties:

• Impatient Man: go with the only options available
• Slow-Witted Woman: greet, then wait.
• Injured Woman: greet, then tell her what year it is (it’s at the top of the screen)

Tips: N/A

Chauncey Wood (Play)

Problem: Needs additional actor for play.

Solution: Does not matter who in the party is the actor. No skill check required. Select the following choices during the play:

• “…Thrace?”
• “…wife?”
• “…revenge!”
• Fight back
• “…Thrace anon.”

Tips: Performing the play perfectly unlocks an additional achievement.

Francis Fletcher (Asleep)

Problem: Francis is asleep in the middle of the trail and needs to be woken up.

Solution: You have several options available. You can: fire a gun (uses 1 bullet), give him coffee (uses 1 coffee), yell at him, kick him, or wait (6 hours). If you don’t have any available bullets or coffee, you’ll have to do all of the other 3 options to wake him up (order does not matter).

Tips: N/A

John Pritchell (Naked)

Problem: A naked man will be standing behind some shrubbery.

Solution: Provide him with 1 clothes.

Tips: Always keep clothes in inventory, otherwise you will not be able to assist him.

Joseph Holman (Murder Mystery)

Problem: Joseph is investigating a murder but wants you to solve it.

Solution: You don’t NEED to do all of the investigative work, but you can if you’re so inclined. Answer with the following:

• “Make accusation”
• “Marshall Brennan”
• “Continue”
• “Not right-handed”
• “Bruise”
• “Wasn’t muddy”
• “Wasn’t raining”
• “He was interrupted”
• “Thefts’ mastermind”
• “Continue”

Tips: N/A

Obadiah Oakley (Riddles)

Problem: Must pass 3 riddles.

Solutions: Here are the ones I’ve seen:

• What runs, but never walks. Murmurs, but never talks. Has a bed, but never sleeps. And has a mouth but never eats? (A river)
• What is 3/7 chicken, 2/3 cat, and 2/4 goat? (Chicago)
• What is greater than God, more evil than the devil; the poor have it, the rich need it; and if you eat it, you’ll die? (Nothing)

Tips: All of there are easy to Google if they aren’t on this list.

Ralph L Kilbourne (Indebted)

Problem: Creditors have come for Robert and want $50.

Solution: There are several approaches you can take. Firstly, you can attempt to defuse the situation using your wit, or if you have a party member with a “Charming” personality, they might be able to talk the creditors down. Alternatively, you can choose to pay the $50 owed. Lastly, if you prefer a more confrontational approach, you can opt to fight the creditors. Regardless of your choice, all of these options will ultimately result in the creditors leaving.

Tip: If you decide to pay the initial $50, be aware that the creditors may try to persuade you that Ralph actually owes them $75. If you agree to pay the $75, it will deduct AN ADDITIONAL $75 from your funds, rather than just the extra $25. So, it’s essential to be cautious when making this decision.

Robert Moore (Wagon Rider)

Problem: Robert does not want to walk the rest of the way to the next stop.

Solution: Robert will hop in the back of your wagon, and you will need to clear room for him. He takes up a total of 7 spaces (3 tall, with 1 in the top row, 2 in the middle row, and 4 in the bottom row). If you discard him from your wagon, you will not receive the medallion. You must carry him until he jumps back out of your wagon (only like 10 miles)

Tips: It is highly recommended to NOT attempt to do a Dragoon Medallion run on the same run you’re doing the antique clock or using the Wind Wagon unless you are a pro at managing your space. It becomes a tight tight tight squeeze.

Sidney Smith (Injured)

Problem: Sidney misfired his rifle and is injured.

Solution: This is a two part event. You will need to provide Sidney with 1 medicine the first time you see him. He will not give you the medallion at this time. Go to the next Dragoon waypoint and he will be injured on the ground again. Give him another 1 medicine and he will give you the medallion.

Tips: Keep at least 2 medicine on you at all times until you complete both waypoints for Sidney.