A "Happy Birthday Windows" How-To: Install Windows 3.1 on a Virtual PC

Alex Castle

Today is (believe it or not) the 25th birthday of the Windows operating system. To celebrate, we’re going to take a little trip back in time, and relive the glory(?) days of Windows 3.1. Windows 3.1 was a lot of people’s first exposure to Windows, but there are also a lot of younger computer fans who never got a chance to try it out. In this mini-how-to we’ll show you how to get a virtual Windows 3.1 sandbox up and running, using free, virtualization software VirtualBox.

So whether you missed out on trying the earliest popular version of Windows, or you just want to take a little nostalgia trip, read on!

What you’ll need

It’s actually not incredibly hard to create a Windows 3.1 virtual PC, as long as you have everything you need ahead of time. Here are the things you’ll need to follow along with this how-to:

Installation disks for DOS and Windows 3.1

Windows 3.1 was the last version of Windows that was just a graphical frontend for the DOS operating system. That means that in order to install it, we’ll have to install DOS first and you’ll need the installation disks for both. If you’ve got your old installation disks still lying around, you can use those, but it’s even more convenient if you saved them to your hard disk as an .IMG file at some point in time. Both Windows 3.1 and DOS have been off the market for a very long time, and (you didn’t hear this from us) installation disks can be easily found for download at places around the internet.


There are several different options available for running a virtual PC, but our favorite recommendation is VirtualBox—a free virtualization software package owned by Oracle. To get it, just go to VirtualBox.org , click on the downloads link, and select the latest version of VirtualBox for Windows Hosts (assuming you’re running Windows, that is). The VirtualBox installer is straightforward, so get it installed on your system before we go any farther.

Step 1. Create your virtual PC

To get started installing Windows 3.1, we’ll first need to “build” a virtual PC for it to run on. Fortunately, VirtualBox makes this process a lot easier than building a new PC in real life. To get started, just click the New button in the upper-left-hand corner of VirtualBox.

The New Virtual Machine wizard will pop up. At the first options screen, you’ll be asked to give the PC a name and select its type. For a name, we suggest “Windows 3.1” and for it’s Operating System select “other,” and for Version select “DOS.”

The default memory size of 32 MB will be fine. When asked about which hard drive to use, select Create New Hard Disk and then choose Dynamically Expanding Storage. The default size of 512 MB will be plenty for your Windows 3.1 system (and don’t worry, the virtual hard drive will not actually take up a half-gig of your real hard drives space, unless you manage to use up that much in the virtual Win 3.1 PC.

When you’re done with the New Virtual Machine wizard, the new machine will appear in the list at the left of the VirtualBox window. (Yours won’t have the Ubuntu machines in the screenshot—that’s just us. Virtual Box is an excellent way to try out Linux, by the way.)

There’s one final thing we have to do to our Virtual PC before we can begin installing DOS. By default, a virtual PC does not have a floppy drive, so let’s change that.

Select your Windows 3.1 virtual PC, then click on Settings. In the settings, click on the Storage tab, and then click the small Add Controller button under the list of storage locations. Select Add Floppy Controller from the list.

Step 2. Install DOS

While you’re still in the storage settings menu, click the button next to the floppy controller that looks like a small floppy disk with a plus sign on it. This will create a new floppy drive accessible to your virtual PC. Click on the new floppy (initially marked “Empty”) and on the right side of the window, click the small folder button next to the dropdown marked “Floppy Device.”

This opens the Virtual Media Manager, which is a list of virtual media available to be inserted into your machine. By default, this list will be blank, so lets fill it out a little bit.

Click on the Add button. This will open a browser which lets you find additional .IMG files to add to your virtual media collection. Navigate to wherever your DOS install disks are located, select all of them, then hit OK. Do the same for your Windows install disks.

Now that you’ve got a list of all your disks, click the first DOS installation disk and click Select. You’ll see in the storage settings menu that that disk is now loaded into your virtual PC’s virtual floppy drive. Click OK to exit the setting menu.

You’re finally ready to fire up your virtual PC. Select it, then click Start. If you’ve done everything right, the DOS installer will start with your new PC. Simply follow the instructions on screen.

When you’re installing DOS, the installation may hang at “Formatting Drive C:” If it does this, you’ll need to do the following:

1) Reset your virtual PC

2) Hit the F8 key as the box loads

3) You’ll be asked if you want to load individual files. Agree to the first file, then choose not to load AUTOEXEC.BAT

4) Type format to manually format your C Disk (of course, remember that this is just the virtual machines C disk, not your actual PC’s.

5) Type setup to resume the DOS setup.

When DOS is installing, you’ll be asked to switch out CDs. To do that, first release your mouse by pressing the right control key, then click on the Devices menu at the top of the window, select Floppy Devices and pick the next install disk. You have to do it this way because while the machine is running you cannot access the settings menu.

Finally, your DOS installation should be complete.

Step 3. Install Windows

The final step is to install Windows itself. This is actually pretty straightforward. Just switch the floppy disk the same way, selecting the first Windows install disk, then navigate to your floppy drive in DOS by typing A: and hitting enter. Finally, enter the command setup to run the Windows 3.1 installer.

You can select the Express Setup option, and then the only other thing you’ll really need to do is switch out the floppy disks, like you did with the DOS installer. You’ll be asked for your username in the middle of the installation, and to verify a few other options, but that’s pretty much it.

When Windows 3.1 starts up for the first time, you’ll be given the option to take a pretty hilarious tutorial about how to use a mouse. If you decline, you’ll be asked to restart your computer.

After you restart, you’ll find yourself back in DOS. To get back into Windows, type win.

And that’s it. You’re now getting the full Windows 3.1 experience. Check out the astounding visuals, marvel at the lack of a start bar and think deeply on the fact that just 18 years ago we thought this was pretty darn cool. If you want to complete the experience, find some old games on floppy images, and try running them through Windows.

Around the web