The “free shareware” thing is kind of back. I’ve been noticing more and more games producing demos; check out Steam Next fest, for example.
I also remember playing a ton of games from a CD. I had a Mac at the time, but it was “dos compatible”, which meant it had a 486 in addition to the Mac processor at the time, so you could switch over into dos, though you could only allocate half the ram to it.
We ended up installing Windows 95 to play a lot of the games, which ran great on the available 4 MB of RAM.