What’s a geek to do with VMware, extra hard disk space, and RAM to spare?  Why fill it with all the operating systems he can! For the fun of it, we take a look at virtualizing a classic version of Windows. 

We start with one of the first popular version of Windows – Windows 3.11.  Many of us can remember using Windows 3.11, but may be surprised to go back and see how many things still function similar in today’s versions. Here’s some screenshots of Windows 3.11 running in VMware Player on Windows 7 x64.  Yes, that’s a 16 bit OS running on top of a 64 bit OS.

Windows 3.1

The installer looks surprisingly familiar … hey, it looks just like the initial stage of XP’s installer.

Yes, we still have to start Windows by entering “win” at the command prompt…

The famous 3.1 boot screen … looks a little different than the Vista or 7 startup animation.


Do you need to learn how to use the mouse? I was actually using a Microsoft Wireless mouse in Windows 3.11, since it just looks like a standard PS/2 mouse through VMware.

Welcome to Windows 3.11.  No exit buttons; just double-click on the left-hand side of the Window.  Amazingly, you can still exit programs this way in all other versions of Windows, including Windows 7.

The great-granddaddy of Windows 7 Libraries…

The infamous Paint…formerly called Paintbrush.

We’ve all wasted countless hours on Minesweeper…

There wasn’t the ability to save documents to a whole lot of different formats back then.

But don’t forget, we’re running it inside Windows 7.  Hey, it looks pretty good in Flip 3D…

Oh, and don’t forget to exit Windows when you’re done for the day … it was basically just a program that is running on DOS.  Clicking Exit doesn’t shut down your computer, it only exits to DOS.


We hope you enjoyed this trip down memory lane…those of you who are old enough to remember that is. Leave a comment below and share your Windows 3.1 stories. We remember this was quite a defining moment in computer geek history when it was launched.

Matthew Guay
Matthew Guay is a veteran app reviewer and technology tip writer. His work has appeared on Zapier's blog, AppStorm, Envato Tuts+, and his own blog, Techinch.
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