The Yukon Trail (Windows 3.1)

The game starts in Seattle in August 1897 (right before the actual Gold Rush). The player is presented with a town with a wharf with a ferry and downtown. The game does not allow the player to buy tickets for the ferry, nor are they allowed to purchase food and supplies until they choose a partner: A banker, a carpenter, a native of the Yukon, or a journalist. The partners (except for the journalist) each have unique modifiers: The carpenter can build a boat more effectively, the native can carry the most, and the banker has the most money. The player can then buy equipment and food for the journey (although they do not have to). The player then purchases a ticket on one of three ferries (each with varying reliability, with the corresponding cost) to either Skagway or Dyea. There is also a peddler who will sell one of various items, including "gold-sniffing" gophers, a trail bicycle, eggs, and caviar or kittens. Some of the peddler's items are relatively worthless, but others may be resold at a profit. The player's partner can offer advice in all of these matters, but it is not always wise to heed their advice. For instance, some partners will encourage the player to delay buying supplies until they arrive in Alaska, where supplies turn out to be more expensive, or to buy the peddler's worthless items.
The Trail

Once the player gets a ticket, they head to the wharf where, depending on the ferry, they either board immediately, wait a week, or wait two weeks. Once in the town (either Skagway or Dyea), they can purchase any supplies that weren't bought in Seattle (albeit at an increased price), gamble, or head for the trail.

The Yukon Trail gives children plenty of opportunities to think about the situation, giving many options and many possible consequences for each event, thus building problem solving skills. The initial choice players make on the trail, and can constantly change if wished, is the load they personally carry. A smaller load resulted in the ground moved each day to become somewhat shorter (as some of the supplies have to be left behind and then returned for). Moreover, the trail becomes much more difficult to travel when encroaching upon the winter months. However, a larger load will result in a higher probability of the player or their partner being injured.

Midway through the trail, the player stops at a camp. They can then purchase (or sell) goods before heading to the Canadian border to pay a toll to pass to the Yukon Territory.

Along the trail, numerous random events can occur. Random events include: someone being injured (resulting in the player deciding whether he wants to continue at a slower pace or resting), banditry of goods or supplies, and sudden inclement weather.
The River
Five Finger Rapids seen from Klondike Highway

Once the player arrives at the border, they will be allowed to pass if he has a certain amount of food. Then, the player arrives at Bennett Lake after a short amount of hiking. While there, they meet the legendary Mountie Sam Steele. They are allowed to build one of three boats. Once the lake has melted, the player can go on the river with their boat. When spring does come, depending on how soon you arrived at Lake Bennett, Sam Steele will let you depart right away, or have you wait two or four days before departure.

On the river, the speed is determined by the type of boat chosen. There are several minigames, which involve guiding your boat out of rocks and whirlpools. After the minigame, if the player's boat has been damaged, he can choose to repair the boat or build a new one from scratch.
Jack London in Dawson City

The river will eventually lead the player to Dawson City, where they are presented with a list of areas they and their partner can claim. There, they meet author Jack London, Nellie Cashman, and another woman named Belinda Mulrooney. Once they have claimed an area, they can begin searching for gold. Once it becomes winter, the gold searching stops and the player's score is tallied by the amount of money he has (from the entire journey, including the gold at the claim). Most claims will yield small amounts of gold, but #1 Above Bonanza Creek and #1 Below Bonanza Creek allow you to strike it rich.
Landmarks

Periodically, the player stops at landmarks along the journey, where players can learn historical facts about each location. Some include the Dead Horse Trail, the totem poles, and the three rapids: Miles Canyon, White Horse Rapids and Five Finger Rapids.