Try to take down a buffalo or a bear while hunting. If the river is deeper than 2 feet, float the wagon or use a ferry instead of fording it. Don't run out of ammo or food. Simply keep one extra component of each type on hand. When you need more bullets, eat some cookies or candy.
You can also win by reaching the end without dying. However, this isn't easy because the game has no pause button. Once you enter a scene with danger, you have to stay in that scene until you die. You can't reload your character and start over again without losing all your progress toward winning. If you want to try this method, make sure you have a safe place to retreat to when you need to recharge your supplies. For example, if you get attacked by Indians, go hide in a cave or under a tree. They'll be busy killing you enemies so they won't attack you first. After they're done, come out from cover and see what's left of you.
There are also lots of items you can collect along the way that will help you survive. These include gold nuggets, which can be used to buy weapons and tools at trading posts; ammunition, which you can find hidden around the map; and food, which grows naturally in certain areas. Try to search every square inch of the ground when exploring ruins or abandoned buildings because sometimes items are buried beneath debris.
You can only take 100 pounds of meat every day, and you can only have 2000 pounds of food in your wagon at any given moment. Even yet, if you're aiming for a high score or are running short on food, hunting is at least as useful as relaxing. You can eat almost anything that grows or flies or crawls or floats down off a tree. Meat is the most important food, but plants provide essential nutrients like vitamin C and B12. Starchy foods like corn, wheat, and potatoes are also important to have on hand.
In fact, having too many resources can be just as bad as having nothing at all. If you have lots of wagons going down the same road, tensions will rise. Attacks will occur. Wars will break out. The best way to avoid trouble is by being aware of your surroundings and knowing when to keep quiet and stay away from conflicts.
You should always have enough food to last you through one full game season. That's about three months in the wild and five months in the cities. Of course, if you get sick or lose anyone to starvation, you'll need to feed them beyond what's considered normal so they don't suffer. But even so, it's best to make sure you have enough food for more than just two people.
The truth is, you can only carry such a limited amount of food on the trail because it's expensive to transport.
When you first start the game, you should buy the following items: 5 to 10 boxes of ammunition, 2 oxen, 2 sets of clothing, 1 of each spare part, and 75 pounds of food. When the trail begins, hunt once a day (for big game) until the animal is sparse, then switch to every other day. As soon as you enter any town, sell your goods and divide your money among yourself and your team members. You can now travel farther down the road with less effort so instead of using up all your energy hunting, just walk into town and pick up some more supplies.
The most important thing to remember when shopping is to always be prepared for anything because this adventure isn't going to play out like a movie. It's about survival of the fittest so you need to keep yourself ready at all times by planning ahead.