I found a great old game that I used to play back in the day. It's the Hitchhiker's Guide To The Galaxy text adventure. It took me a while to get it working in 7, and damn it can be frustrating at times, but it's still awesome.
As for Windows based games, Monty Python and the Holy Grail is hilarious, and there was some old text based game that ran on 3.11 where you were driving along and shooting elephants and other wild animals with rockets and stuff, but I can't remember the name of it.
Oregon Trail was fun in school computer lab too.