DOSBox with Windows 3.1 is the easiest way.

I have had performance issues with Dosbox running 3.1 for some 16bit games. I found it better to run either Windows98 or Win XP in VMware or Windows own Virtual Machine for those games.

Windows XP in Virtual Machine is probably the easiest and quickest to setup and use. Also you can have own program shortcuts directly in Windows 7 that starts up the Virtual Machine and then the program.

Gotta try DOSBox with Windows 3.1 then. Never tried this before but how do I add the games there?

Windows 3.1x DOSBox Guide

Install the games through Windows 3.1 if they require an install.

I tested several 16bit Windows 3.x games on Windows 8 64bit today using DOSBox.

Windows 8 no longer supports VPC 2007 or VPC for Windows 7 and 9x support in Vmware 8 seems kind of flaky (May have been the install tho).

MadMonk wrote:

I'd like to play games like Moraff's Escapade, Chip's Challenge, Castle of the Winds and Kye again without trouble.

Some of those (Chip's Challenge and Kye have pretty big fanbases, as I recall) probably have newer, 32-bit versions available in one form or another. Others (Escapade in particular, I think) might already be 32-bit but have 16-bit installers, such that you just need to find an unpacker.

Hey, got the games working but I'm getting an error when trying to run the Escapade installer(?). You can check out the app if interested. http://games.lisisoft.com/full-download-game/ … s-escapade.html

Perhaps you should try running it from its own folder instead of the Windows directory? (Putting random things in C:\WINDOWS has never, ever been a good idea.)

It also has a MS-DOS label.....if it's a DOS program run it in DOS.

Found the 95-version of the game from an old CD and it works fine in Win7.