Oregon

For me, the 1985 Apple II version will always be the definitive version of Oregon Trail. It's important to note that there were two variants of Oregon Trail on the Apple II, and the one that most people know is an independant 1985 MECC release that let you name your traveling members, manage your pace, and let you ford rivers. There was another Oregon Trail before that, from 1979, and it is featured in a MECC compilation called "Elementary Vol. 6", where "OREGON" is just one of many similar text-based simulations. Compared to the lavish 1985 release, the 1979 Oregon is very streamlined. You don't get to name family members, you can shoot bandits this time around(no aiming necessary, just one-button timing), and as a whole the experience is much easier.

The game, though? It was very easy to make management sims in the earliest days of computer games and what's magnificent about Trail is how still functional and fair it is even after four decades. The descisions you make feel natural and intuitive and even if you can't crack the statistics formula in RPGs you still get an idea of what you're doing, and chances are you'll have palpable and manageable results coming from them. An absolute essential and classic that'll have you relish in the struggle of traveling.