How to run Windows 3.1 software on Windows 10 & 11 (64bit) & Linux

Because... because... why not?

Modern, 64bit versions of Windows… don’t support running Windows 3.1 software.

Linux distributions can’t run Windows 3.1 software either. (At least… not out of the box.)

This is, obviously, a tragedy. How on Earth are we expected to play Castle of the Winds or SkiFree on modern operating systems!?

Luckily, Wine does an astoundingly good job of supporting Windows 3.1 software… though many might not realize it (as most people are focused on the support for Windows 95 and later software).

On Windows

If you’re on Windows, you’ll want to grab a copy of Winevdm — a version of Wine specifically for running Windows 3.1 software on modern 64 bit Windows. Free and open source. Good stuff.

Installation is dog simple. Run “install” and — shazam — you can now run Castle of the Winds on Windows 10 / 11. Along with just about anything else you might like.

I don’t use Windows very often. But, when I do, I darn well better have access to Castle of the Winds and SkiFree. Darn it.

On Linux

Things are even easier on Linux. Simply install Wine from the default repositories for your distribution.

On Debian (and Ubuntu, etc.):

sudo apt-get install wine

On Fedora:

sudo dnf install wine

On Arch:

sudo pacman -S wine

Whamo. You’re good to go.

There are other ways…

Using Wine to run Windows 3.1 software (either on Linux or Windows) works fairly well for the majority of software out there. But, occasionally, you’ll run into snags.

Sometimes… some pretty big ones.

For those instances, looking at running Windows 3.1 in a dedicated emulator (such as QEMU, VirtualBox, or DOSbox) is going to net far more desirable results.

But, if the software you need runs in Wine, that route will give you the most “seamless” experience… as the software will run, in its own window, alongside the rest of your software.

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