The Oregon Trail/Walkthrough
There are three difficulty settings:
- Banker ($1600)
- Carpenter ($800, 2× points)
- Farmer ($400, 3× points)
There are no differences other than the starting money and the points bonus at the end of the game. The farmer is by far the best choice for a high score. Try a run through the game with banker, first, to get the hang of it. It may seem tough, and doing well as a farmer might seem impossible. But it isn't! With the proper strategy, random events should be your only problem and they should not keep you from at least making it to the end of the game.
 When to start?
It's better to leave too early than too late, because if you do leave too early you can burn time (at the cost of resources, though). If you leave too late, you'll have to face winter, although it should not be a problem unless you leave in July. If you're going to do a lot of hunting, or travel at a slow pace often, leave in May; otherwise, leave in June.
 Buying stuff
Of course, what you buy depends on your profession. If you're a banker, you can start with such luxuries as:
- 9 yoke (18 oxen)
- 2000 pounds of food
- 20 sets of clothes
- 3 of each spare part
As you can see, if you want a really easy game choose the banker. How many boxes of bullets you take is up to you (but you really won't need more than 20 to start with), but because you're rich, you don't need to hunt. You can just buy more food at the forts along the way. It'll be more expensive then, of course, so replenish your supplies early and often.
On the other end of the spectrum is the farmer. If you want top points, which you probably do if you're playing a farmer, you'll want something more like:
- 3 yoke (6 oxen)
- No food (hunt for it instead)
- 15 sets of clothes
- 20 boxes of bullets
- 2 of each spare part
This leaves you with $30, which you can use for ferries or to buy more supplies in case you need them. The rationale behind hunting is that one box of bullets is 20 bullets for $2.00 (at the start of the game), so each bullet costs 10 cents, and every bullet has the potential to bag up to 100 pounds of food, so hunting is far more economical.
You can change this arrangement around a little, but you definitely need at least 3 yoke, 10 sets of clothes, and 2 of each spare part.
 And we're off!
This walkthrough focuses on the farmer with the supplies covered above. The Banker and Carpenter play similarly, although supplies referred to below may not be part of your default supplies.
Set your pace to "grueling" and your food consumption to "bare bones" before leaving Independence. Then after you leave, hit Return before you actually move. If you bought supplies similar to the above you've started with little to no food. Hunt until you get 2000 pounds of food, which is the maximum your wagon can carry. This will probably take a little over a month in game time. When hunting, do not bother shooting small game like rabbits; they're not worth the price in points. Even though you have 2000 pounds of food, keep going at grueling/bare bones until your health starts to really suffer. You want to have about 2000 pounds at the end, too, and you don't want to spend too many bullets in between. If you shoot a buffalo (or later in the game, a bear), don't fire another bullet; you have enough food. Same if you shoot two deer. You can never carry more than 100 pounds of food back to the wagon, so further bullets will be wasted. If you waste too many bullets, they will add up and subtract from your score.
When you reach the Kansas River Crossing, check the water level. If it's 2.5 feet deep or less, it should be safe to ford the river. Otherwise, you can either float the wagon or take a ferry. If you float the wagon and something goes wrong you can just reset the game (since you're near the beginning), but you might not want to since to spent so much time hunting. If so, go ahead with the ferry, bearing in mind it will deduct a point from your final score (two points for carpenter, three points for farmer), as $5.00 is one point.
At the Big Blue River Crossing, you cannot take a ferry. You must ford, float, or wait for conditions to improve. As before, ford when the water level is 2.5 or less. This may well be the last time you can safely ford a river!
You can safely ignore all forts and other landmarks (but you may want to buy supplies at a fort if something goes wrong), other than rivers which must be passed. So you will pass by Fort Kearney and and Chimney Rock. Fort Laramie is special because it marks the point where you flip the disk to the other side. After Laramie, your progress will be slower, as well, and you will no longer find any buffalo, but you'll find bear instead.
Continue through Independence Rock to South Pass, where you have the option of going to a fort or to a different landmark. In these situations, the other landmark is preferred because the fort is out of the way, unless of course you need to buy supplies. Therefore, you will continue to the different landmark, in this case, the Green River. If you don't like the thought of crossing another hazardous river, go ahead to the fort; you should be able to take a ferry here, and you would be wise to do so. At the Snake River, hire an Indian guide in exchange for clothes. Pass Fort Boise, then the Blue Mountains. Again you'll have a divided trail; head to The Dalles. There, take the river and play the easy minigame and you will arrive in Oregon!