Easy money...
	Fine Whip...
	Red Wagon...
	Various Trophies...

Go to the post located at each fort and begin the mini-game. Intentionally lose just before the mini-game ends. You will be prompted if you want to play again for a bonus. Select "No" to return to the fort with $1 for each correct tap you had previously made. Repeat the process to earn as much money as desired.

Complete a segment of the trail without hitting any obstacles.

Kill your first animal.

Complete each requirement to get the specified trophy.

Trophy	How to unlock
24 Karat	Finish the Gold Rush storyline.
Alpha Male	Fight off a wolf attack.
Bridger to Nowhere	Arrive at Jim Bridger's Trading Post.
Careful Driver	Complete a segment of the trail without hitting any obstacles.
Classic Complaint	Have one of your passengers catch dysentery and don't administer medicine for it.
First Time Through	Get to Oregon for the first time.
Full House	Get to the end of the trail without losing any family members.
Have Gun, Will Shoot	Kill your first animal.
Hypochondriac	Use medicine on one of your sick passengers.
Journeyman	Score more than 120,000 points in a chapter.
Left Behind	Hunt for more than 150 pounds of food in one day.
Lickety Split	Arrive in Oregon with at least 45 days remaining.
Love Conquers All	Finish the Family Affair storyline.
Master Fisherman	Catch 60 pounds of fish in one day.
Piano Man	Bring the piano as your heirloom and complete the journey to Oregon.
Reel Talent	Catch your first fish.
Third Wheel	Break and replace two wagon wheels in one segment of the trail.
Trail Master	Score more than 150,000 points in a chapter.
Triple Threat	Finish the Three Brave Brothers storyline.
Uncivil War	Finish the Stuck in the Middle storyline.
Victimized	Get robbed 10 total times in one trip down the trail.
Walla Walla	Arrive at Walla Walla, Washington.