http://www.hotud.org have a lot of old games for free ( Ultima V , underground) . I believe it is legal too.
Home of the Underdogs is awesome, but it's not really a legal site. It has flourished in the wake of old game developers and defunct studios, and was really important to maintaining and patching those games. But now, with sites like GoG or even Steam, the old games have some value again. So better to pick up the games cheap like this so the devs are still supported.
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