The Oregon Trail – All Dragoon Sighting Encounters Guide

Guide to all the Dragoon Sighting encounters on the Oregon journeys.

Guide to All Dragoon Sighting Encounters

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All Dragoon Encounters

The list below is in alphabetical order after the quest-giver, however, the Dragoons will appear in a random order in the game. These turn up between Fort Kearny and Fort Boise (legs 2 – 4). It is not possible to hit all the Dragoon waypoints that spawn, but going down the path with the most spawns will get you all 10 medallions. If you skip any Dragoon waypoints, you will not reach all 10 needed.

Fun Fact: All of these guys are real people who actually existed. The Peoria Party split up into several groups that each went their separate ways; they never reunited.

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: You have a few options here. You can talk them down with high wit or a party member with the “Charming” personality, pay the $50, or try to fight the creditors. All of these options will result in the creditors leaving.
• Tips: If you pay the $50, the creditors will try to convince you that Ralph actually owes them $75. If you agree to pay the $75, it will take AN ADDITIONAL $75 out of your money instead of just the extra $25.

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.