What does HackerNews think of winevdm?
16-bit Windows (Windows 1.x, 2.x, 3.0, 3.1, etc.) on 64-bit Windows
Have you heard of or tried "MS-DOS Player"? It seems to convert binaries into a format that Windows can understand. I think you have to do it on a per-file basis so it might be more of a headache than it's worth; but it's out there!
http://takeda-toshiya.my.coocan.jp/msdos/index.html (original site)
https://virtuallyfun.com/wordpress/2011/02/11/ms-dos-player-...
[edit]There's also winevdm which can run 16 bit windows binaries on 64 bit windows. It has DOS support but it's incomplete and it points back to MS-DOS player in it's readme...
Fun fact, you can use a WineVDM-based 16bit emulator on Windows[0] that translates 16bit calls to 32/64bit calls and install it system-wide thus allowing the use of 16bit programs in 64bit Windows. Here are two examples from screenshots i have around: Microlathe[1], a small utility to build 3D models by rotating a line around an axis (i also made my own clone[3] of it) and [2]a free Smalltalk environment (Smalltalk Express - which i actually consider one of the simplest Smalltalk environments since it only contains a small subset of what you'd find in a modern one thus making it easier to grok).
[0] https://github.com/otya128/winevdm
[1] https://i.imgur.com/e26mqWP.png
Now to see if I can get it running on 64-bit Windows[3], it being a 16-bit Windows game.
[1]: https://www.mobygames.com/game/castle-of-the-winds