The game follows you in 1897 as you set off to the Yukon to make your fortune in gold. You start in Seattle, where you take a ship up to Alaska, travel by foot to the Canadian border, travel down to Bennett Lake in British Columbia, build a boat to traverse the Yukon River itself, and arrive in Dawson City. And with the information you acquired during the trip and a fair bit of luck you might just strike it rich.
Like in The Oregon Trail the challenge comes from properly planning your journey to deal with problems both expected and unexpected. You got to time your journey correctly and make sure you have the right supplies. The difference is in the level of interactivity you have on the trail. Each town you visit has several characters you can click on and talk to, all with their own stories and advice on how to reach Dawson. Some of them you might even run into multiple times. The game teaches its players all about the hardships of the Klondike gold rush, the preparations that were needed, the problems stampeders faced, famous locations, and historical figures who were involved.
The Yukon Trail contains examples of the following tropes:
- Betting Mini-Game: There is an addictive card game you can play in Dyea, and a three-card monte game in Skagway which is a scam.
- But Thou Must!: Picking a partner is required and the game won't let you buy an outfit or a ticket until you've done so.
- Cash Gate: The border to Canada functions in a similar way. If you have not brought enough food to the border by the time you reach it you are sent back to the last camp you visited to buy more.
- Gold Fever: A real life version, and everyone you meet has it. One person you talk in Seattle complains the town is practically empty because of it.
- In the Past, Everyone Will Be Famous: On your one journey to the Yukon you just happen to run into Jack London, Sam Steele, and Nellie Cashman.
- Joke Item: While in Seattle, you can purchase a bicycle, which the seller says will help you on your journey. Should you purchase it, it gets thrown off the side of the ship you travel on to Alaska by two sailors, who laugh at the idea of using a bike on the trail. It doesn't help the fact your partner will suggest buying it in the first place, depending on who you picked.
- Lighter and Softer: There's no risk of death in this game like in Oregon Trail. If you run out of food, you just return home rather than dying of dysentery.
- The Load: Midas T. Golden, one of your potential partners, is a portly Rich in Dollars, Poor in Sense businessman who is practically worthless for the journey as he gives bad advice and is prone to injury.
- Naturalized Name: One of the four partners you can take with you is a native woman who goes by the name Linda for (your) convenience sake.
- Prospector: You play as one, and along the trail you meet many others. The one who introduces the game looks the most stereotypical.
- Random Event: The player can be impeded by several problems which happen randomly during the trip, such as blizzards, food thieves, and broken ankles, and there's no way to prevent them.
- Snake Oil Salesman: You encounter one on the Seattle docks. While he does sell food you can resell later at a markup, he also sells you special gold sniffing gophers, which of course do not work.
- Wretched Hive: Skagway is portrayed like this. You can be scammed in three-card monte, and the authority figure you report it to is in on the scam.