The Oregon Trail

The Oregon Trail

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All Dragoon Sighting Encounters (Going for Gold achievement)
By SecretAgentAu
Guide to all the Dragoon Sighting encounters on the Oregon journeys. All encounters needed for the "Going for Gold" achievement.
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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.

This will need to be completed 10 different times on 10 different journeys to earn the "Going for Gold" achievement.

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.
1. 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
2. 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
3. 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.
4. 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). You’ll have to do 3 options to wake him up.

Tips: N/A
5. John Pritchell (Naked)
Problem: John somehow managed to lose his clothes and is 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.
6. 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
7. 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)
  • Only one color, but not one size. Stuck at the bottom, yet easily flies. Present in the sun, but not in rain. Doing no harm, and feeling no pain. What am I? (A shadow)
  • I speak without a mouth and hear without ears. I have no body, but come alive with wind. What am I? (An echo)
  • I have branches yet I have no leaves, no trunk and no fruit. What am I? (A bank)
Tips: All of these are easy to Google if they aren’t on this list.
8. 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.
9. 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 usually)

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.
10. 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.
6 Comments
Tarani80 3 Aug @ 7:48am 
i can't get all 10. I tried now for the 6-7th time. Always just get the change to get max 9. Becuase on some ways there are 2 or 3 dragoons but i can't reach all. And then the last psth before the fort no one comes up again.
lkj2534 1 Jul @ 12:52am 
7.오베디아 오클리 부서지지만 떨어지지않고 떨어지지만 부서지지만 않는 것 : 밤 과 낮 입니다.
7.Obadiah Oakley Broken but not Falling, Falling but not Broken: Night and Day.
Spiny 6 Dec, 2024 @ 9:36pm 
You can close the game after receiving the 10th medal but before ending the encounter to keep reloading it. Saves playing the same route 10 times.
thiing2 17 Apr, 2024 @ 1:26am 
Is this achievement still glitching for others too? I just did two play throughs and completed all 10 and still nada :/
Vance Finiraldi 6 Jan, 2024 @ 7:50pm 
For number 2: In Oregon or Bust/Hard Mode, the year you need to give to the old lady for the final question is incorrect. Though the journey takes place in 1850, you need to give the erroneous answer of 1858 (first answer in the second row) to pass. Giving the actual correct answer will result in Amos Cook thinking you've given the wrong year and disqualify you from the medal.
Wandering Mania 1 Jan, 2024 @ 1:29am 
For number 10: If you have a Doctor/Physician class character in your party, you can heal him without medicine.