How-To Geek

Geek Fun: Virtualized old school Windows 3.11

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 digs up tasty bytes about Windows, Virtualization, and the cloud, and serves them up for all to enjoy!

  • Published 02/26/10

Comments (30)

  1. Chris K

    I’m now inspired to create a VM with my DOS 6.22 and DesqView/X floppies. Hmm, I still have my Wildcat BBS floppies too. Could be a fun retro project.

    But first I have to find a working USB floppy drive!

  2. John Kelly

    Windows 1 on an Apricot XEN

    How many clocks can we have “ticking” at the same time?

  3. SanderB

    Win 3.11 was for me just another app on Dos that I used every now and then as a sort of try out. Soon enough though I switched over to the linux camp. It was after 10 years or so that I tried to install a copy of the then popular Windows 98 which didn’t work at first.
    Nowadays I am using a Mac…

  4. Kiran Ghag

    wow! JIT,

    yesterday i spent much time searching old splash screens and screenshots for retro os/apps and games… :) going back in time is fun!

    miss those a lot.

  5. GKI610

    Ah, the memories! Steep learning curve for me at the time.

  6. notusedupyet

    What a flashback, I thought of the 30 (I think ) or so 3.5″ floppies it took to install it. And if any screwed up you had to start over. even on number 29. Also you could just make copies of the floppies and you had another copy of Windows 3.1

  7. Oh, THAT Brian!

    OK – I have legitimate access to both of those. How do I get started building it up?

  8. rew

    where can I download windows 3.11

  9. Rich Schinnell

    I have been running WWG 31.. for over 5 years on the VPC from MS. I even ran it on a MACintosh under the VPC for mac.

    I have screen shots of web pages that I accessed with windows 3.11 if your interested.

    The first time you create the hard disk for the vpc and windows to install dos 6.22, it can get
    a bit intimidating using fdisk and format c:/s I had to keep looking at my real c drive to make
    sure that I was not going to explode. but it is fun.
    I have installed almost all versions of windows and linux on the windows 7 vpc which works
    fine. There are a few gotcha’s that you have to watch out for. Like the cursor being captured
    by the dos/windows session. but ctrl+alt+del allows you to go back properly. I have even
    used the printers from dos and windows.


  10. Dane

    Wasn’t all that long ago I decided to start up MS Bob in a VM. That really took me back…

  11. talmont

    *sniff* Windows with Networking, they had to distinguish it!!!

    Now I need a good cry….

  12. leoDb

    “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.”

    Man! I have been using Windows since the 3.11 and never, ever noticed this trick! :) I feel ashamed of myself.

  13. Bill

    OK so where do i go to get it and how do i install it and do i have to pay for it?

  14. Aeiluindae

    As a kid, I remember getting annoyed when they changed the name from Paintbrush to Paint. We were stuck with Windows 3.1 for a remarkably long time due to OS upgrades being difficult to find in the DRC (formerly Zaire). Computer viruses were not exactly a pressing security issue, however. That any computer lasted as long as that laptop did in the African rain forest (100% humidity, bugs, dirt, water) still amazes me. Two laptops in 8 years, with a motherboard replacement in each and I think one got buried in a crate under a house during a civil war for a couple years. We still have the second one, running Windows 95. A few weeks ago, I found out that an old favourite game was available for Linux. Best nostalgia day ever.

  15. clcamp0331

    Ahhhh. MEMORABILIA……. Windows 3.0, Windows 3.1, Windows 3.11, which all were Program Manager, then after it seemed like forever the Granddaddy of the Start Bar was, I remember it well ” Windows 95″ a very big milestone, that ridded itself of Program Manager and along came Explorer! Well all you (me included) old gramps remember everything that came after. Its been a very long journey to Windows 7. Its funny though, you would think by now all computers would be like the ones on Star Trek with the beautiful intelligent voice. I guess sometimes progress is just slow. But all in all I do give Microsoft some credit where it is due.

    Power to all the Windows users

  16. anon

    You know, those pictures remind me of all the “wasted” years spent with Windows. I’m glad to have left it behind for much more interesting stuff (like gnu/linux, freebsd). Windows is so limiting and uninteresting. DOS was kinda cool and geeky still. Nowadays I don’t even want Windows for free. If I get a computer with Windows I usually wipe it away and install something decent.

    But surely MSFT is happy about people like you 8)

  17. damiththa

    wow windows 3.1, that was my very first OS, bringing back memories.

  18. merry

    I have it and 95 running in an emulator on my iphone
    slow but mainly works
    funny old world

  19. Joe

    I just love the screenshot of it on the flip3d thingy on windows 7, it shows beautifully the transformation from old to new.

  20. Ahmer

    hi kiran plz sned urs email add i talk ot by mail hope u dont mind

  21. Mr T

    Thats awesome, almost reminds me of the old OS2 Warp days, you could also run Windows 3.1 within a window.

  22. Jr.

    hahahahah… Awesome!

  23. murat

    nice wallpaer :D

  24. Sava

    Hehe … so … can you spot the difference between Windows 3.1 and Windows 7 ? :)

  25. James

    I have an interesting question.
    How would I get a Windows 3.11 based CD ROM to open in Windows 7?

    James Burroughs, Olympia, WA

  26. Brian

    Win 3.11 runs great in Dosbox as well, and that’s probably an easier way to get up and running than a full fledged VM host. To answer James’ question above, that’s exactly what I did to play my ancient Windows CDROM games.

  27. Kingmidas

    Win 3.1 was my first OS, thinking about it now i think i would find it rather difficult and even unmanageable to work with the same ebb and flow as i find with my com today….but great
    rememberings cant wait for Win 3.19598XproVista10 !!!

  28. Carlos A

    haha i remember those 1st OS was Dos 5.0 then upgraded to Dos couldnt go to windows 3.1 till later that year, because had an 8088. but man those were the days.

  29. Chad

    Was ski-free a part of 3.11 as well? I can’t remember! How fun to have 3.11 running in a VM :)

  30. Servena

    Thanks for writing such an easy-to-undesrnatd article on this topic.

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