2 bit programs will normally run on 64-bit Windows. I, for example, am running Windows 7 Ultimate 64-bit and can play most 32 bit games just fine. I'm not sure Castle of the Winds will work on 7 or Vista since it was made for Windows 95 (or possibly 3.11) the only solution I can recommend is using a virualy machine (ie: Virtual Box from http://www.virtualbox.org/) and find an older copy of Windows you can install in it. (Just for the record, I just downloaded CotW myself today since I found both the shareware and registered portions of the game up for download on the developer's website.)
Good luck finding a solution. (And please post it here if you find one so I can do the same.)