Yes, there's a classic mac gaming server on hotline. You can use www.tracker-tracker.com to find it. Then use frogblast to download stuff off of the server. Of course I'm not sure if oregan trail is now public domain, or if the company that made it still cares. Standard P2P copyright issues (if you even give a ****)...
a very good game, i always died though. i still have my boxes of myst, zoombinis, spelunxe( i thinks that how you spell it) prince of persia 1 and 2, and some other games my mom bought me when i was about 4.