How to Play 16 Bit Windows Games/Applications on a 64 Bit Computer

If you ever found yourself having the urge to play a really old video game or application, and all you have is something like windows 7 or Windows 8, you may run into some problems attempting to get that particular program to work. While a standard 16 bit DOS program may be kind of easy to run with DOSBox, a 16 Bit Windows program may be a little more tricky to actually run. This guide will show you the basics of running a basic 16 bit Windows program.

Important Notice: This guide was originally published by me on ZeroPaid. It is being republished here for the purpose of updating the guide with any new information I can obtain so that some of the more difficult to play games can be run.

When it comes to old 16 bit video games, some of the more knowledgeable people would suggest using Dosbox. Dosbox is a program that emulates the old DOS environment to run old 16 bit DOS-based programs such as video games. Unfortunately, some games require the Windows environment. For users who run Windows Professional, Enterprise and Ultimate, one possible solution is to download and install the “Windows XP Mode” and “Virtual PC”. The reason is that Windows XP allowed users to run old 16 bit video games. As such, running the official Windows XP emulator is a possible solution for you. Unfortunately, if you are running Windows Home Premium, Microsoft locks us out of this capability unless you upgrade your version of Windows. So, attempting to run a 16 bit Windows video game in 64 bit Windows 7 Home Premium is perhaps the most difficult environment to work with. Is it impossible? After years of problem solving, I finally found out that it’s not impossible.

For any 16 bit DOS programs, one may run into this error message:

Our guide on using DOSBox to run these 16 bit programs are typically sufficient for a number of these games. However, if this is a Windows 16-Bit program, you may find yourself with the following error message when trying to boot the program with DOSBox:

For some people, this may be a message that tells them that they have reached the end of the road in terms of compatibility. For quite some time, I was one of those people. However, after years of infrequent digging around, I was able to find a solution to this problem. There are versions of Windows – namely Windows 3.x) that were actually a DOS program. This means that it’s basically a program that runs within DOS. DOSBox allows you to run programs in a DOS environment. This fact makes it possible to run 16 bit Windows games via DOSBox. Here’s how you essentially create an emulated system that can run 16 Bit Windows games:

Step 1 – Download and Install Dosbox

Go to the official DOSBox website and download the latest version of Dosbox.

Don’t worry about installing a frontend. Frontends are simply visualizations of what we are attempting to do. It’s probably best to stick to vanilla Dosbox which is what we’ll be doing in this guide.

Step 2 – Obtain a Copy of Windows 3.1

There are numerous ways of getting Windows 3.1. You could buy a copy or find some mysterious download version off of some torrent site that rhymes with the pilot day. The choice is yours. Either way, you’ll need to get a copy of the contents of the diskettes (or ISO which would save a few steps) onto your hard drive as most modern computers do not have floppy disk drives.

Step 3 – A Little File Management

You’ll need to do a little file management to make your life a whole lot easier. I prefer to work out of a folder directly on the main hard drive to simplify matters. Really, you could place the main folder anywhere on your hard drive, but locating the files can be tedious if it’s on anything other than directly on the “C” drive. Name that folder anything – preferably something that will allow you to remember later what that folder is for. I chose the name “oldgames”

Next, you’ll need a folder that emulates the disk drive. I chose to go into the “oldgames” folder and create a folder called “floppy”.

For now, this is all that is needed.

Step 4 – Mount Your “C” Drive

When you first open up Dosbox, you’ll see this window:

Yes, we are heading straight into the oldschool DOS prompt. Don’t let it scare you, I’ll share with you everything you need to know.

Next up, we need to type in “MOUNT C C:\OldGames”. Remember, we are using the name of the first folder we created earlier here. If you named that first folder “Old” instead, then you’d type in “MOUNT C C:\Old”. Since I’m using OldGames, this is what I see in Dosbox:

Dosbox is telling me that the drive was successfully mounted here. Congratulations! We successfully mounted the hard drive!

Step 5 – Mount Your “A” Drive

The old version operates thinking we have a floppy drive. This is known as the “A” drive. Think of it as an outdated version of your “D” drive (which is typically your CD/DVD drive). Way back then, everything came in thick square disks instead of larger fancier shiny round disks.

Windows 3.1 came in seven diskettes. So, we need to have a way to install Windows 3.1 even though our computer doesn’t have an A disk drive.

So naturally, we want to mount the floppy drive. Remember the second folder we created that was called “floppy”? That’s our next step.

Like the “C” drive, we need to mount the “A” drive. The cool thing is that what we need to type in is very similar to what we needed to type in to mount the “C” drive. If the second folder you named is also “Floppy”, we need to type in “MOUNT A C:\OldGames\Floppy”. It should look like this if we are successful:

Congradulations! We now have a floppy drive on a Windows 7 computer that physically has no floppy drive!

Step 6 – Begin Installing Windows 3.1

At this point, I am assuming you have the contents of all seven diskettes nicely arranged in a folder somewhere on your actual hard drive. If not, you can do so now (no harm in going back and doing this. What is ideal is to have the contents of the seven diskettes laid out nicely like this:

Again, this will make your life substantially easier in this step.

Now what you need to do is go into the folder with the contents of the first diskette and copy it over to the Floppy disk folder you created earlier (I called it “Floppy”) like so:

When the contents are copied over, go back to Dosbox and type in “A:\SETUP.exe”. When you hit enter, you’ll see the following screen:

Simply press Enter and you’ll get this screen:

Simply press Enter again.

Now it will begin setting up Windows. As we can see, the progress for us above has come to 22%.

Step 7 – Swapping Out to Disk 2

When it has finished installing the contents of the first diskette, the setup will ask for the removal of the first diskette and inserting the next diskette.

At this point, you’ll need to remove the contents of your diskette folder (that we named “Floppy”). Once the files are removed, find the contents of the second diskette and copy it over to the “Floppy” disk folder (much like what we did in the previous step. Once the contents of the second diskette are copied over into our floppy disk folder, we go back to Dosbox and press CTRL+F4. This will reset what Dosbox thinks is in all the directories. After that, hit Enter to continue the installation process.

As we can see above, the installation is going along smoothly right now.

Shortly after this, it will prompt you for the third diskette. Again, simply remove the contents of the Floppy diskette folder and copy over the contents of the third diskette. After that, hit CTRL+F4 in Dosbox and hit Enter to continue the installation.

Step 8 – Installing the Fourth Disk

Once you install the third diskette, you’ll be brought to a Windows environment within a Windows environment. To switch between the Windows 3.1 and your Windows 7 environment (because now Dosbox is, in a sense, trapping your mouse), simply press Alt+Tab and you’ll be able to work between both environments.

After it asks you for your name, you’ll eventually be brought to this screen:

The process at this stage is exactly the same. Remove the contents of your floppy diskette drive and copy over Diskette 4. Hit CTRL+F4, click inside the Windows 3.1 environment in Dosbox and continue the installation.

You’ll do the same process of swapping out the diskettes for diskette 5.

It will, at this point, ask you if you would like to install a printer. I simply chose the “No Printer Attached” option and continued. I also skipped the tutorial as well.

At this point, Windows 3.1 will ask if you want to Reboot. I chose to reboot. Dosbox will then close down.

Step 9 – Opening Windows

Now that we have installed Windows 3.1, the next step is to test to see if Windows will run properly. For that, we need to open Dosbox back up.

When we do, we need to mount the “C” drive. For those who don’t want to do any extra scrolling, that’s, again (in my case), typing in “MOUNT C C:\OldGames”.

Once mounted, we need to browse to that directory. That’s simply a matter of typing in “C:\”.

Now that we are on our virtual “C” drive, we need to start Windows oldschool style. We need to type in “cd C:\WINDOWS” and we’ll get the WINDOWS directory:

After this, it’s simply a matter of typing in “win” and hitting enter to start Windows. You’ll, at this point, be transported back in time to computing in the early 90′s!

Step 10 – Running a Game

At this point, we want to see if any old game would work. So, I selected a old video game called “Dare to Dream”. I exited out of Windows 3.1 and dropped the directory files for the game into the “OldGames” directory. Booted up Windows, went into File Manager, found the directory for my game, ran the .exe file and, voila, the game actually runs!

Yes, this is a 16 bit Windows video game running in Dosbox running in a Windows 7 Home Premium 64 bit operating system.

While the game actually runs, there are no MIDI sounds (old sound files used to play in the background of some games) because of lack of sound drivers.

Step 11 – Installing the Sound Driver

Unfortunately, we don’t have any sound. This has to be manually installed. So, we go to the Control Panel.

Next, we go into “Drivers”. This will bring up this window:

We want to click on “Add”. Next, we’ll want “Sound Blaster 1.5″:

At this point, it will ask you to insert disk 4:

Like before, we remove the contents of the floppy directory on our real hard drive (if you’ve been following this guide, the contents currently in there is diskette 5), then CTRL+F4, then continue. If nothing happens, at this point, exit Windows and mount drive A and direct it towards your floppy folder and go back into Windows and try again.

If successful, you’ll get a screen asking for diskette 5. Swap out contents of the floppy directory for diskette 5 and continue. Once successful, you’ll get a new screen asking for ports and interrupts. This part is truly trial and error, but the following settings worked for me (the window in the top left corner means you were able to get the settings correct):

My advice in determining the correct setting quickly is to pay close attention to the error messages. If the error mentions that the port isn’t correct, change the port. If the error message says the Interrupt isn’t working, it means the port is correct, but the interrupt is wrong.

At this point, you will be asked to restart Windows. Go ahead and restart:

Since restarting Windows 3.1 in a modern computer is almost instant, you’ll probably notice that a restart is pretty much instant. If you hear the old Windows chime, then that probably means you successfully installed the sound driver. If you want to be sure you were successful, you can go into the Control Panel and go into “Sounds”:

Now, you really only need to click on the “test” button to make sure that the sound actually worked. If all went well, you should hear the sound effect you selected:

If you heard anything at all, congratulations! You have sound!

Step 11 – MIDI Mapping

MIDI seems to be a little buggy, but I can show you what worked for me. You need to configure some MIDI settings because old games often used highly compressed MIDI files as background music. First, go into the Control Panel and click on the MIDI Mapper:

In the MIDI settings, I selected “General MIDI”. When I tested the audio for the game “Mordor – The Depths of Dejenol”, I still got error messages and it occasionally crashed Windows 3.1, but despite the error messages, the music still played. There may be better settings to use in the mean time, but for now, these settings worked:

As a general note for the game “Mordor”, you need some additional files to get the game to play properly. Simply download the compressed file available on the Mordor fan site here and extract all the files to the “WINDOWS/SYSTEM” folder in the Windows 3.1 directory. In addition, you’ll need to extract the file “WAVMIX.ini” file into your WINDOWS directory. This should allow the game to at least open up properly.

If Mordor crashes Dosbox, simply remount the A and C drives and go back into Windows again alternatively, simply find the settings that play the MIDI files and deactivate the MIDI sequences. This could add some stability.

Step 12 – Fixing the Video Display

This step was a bit of a pain to figure out, but thankfully, there is a solution that is easy to follow. If you ran any game in Windows 3.1, you may have either noticed that the colours aren’t that great or an error message pop up that said that this game runs better on 256 colours. There is a way to fix this (and even adjust the resolution of Windows to something that is more suited for your current display.

The problem here is that what is running is VGA. There isn’t enough colours to make some of the pictures display properly. While you may be tempted to start digging around in the Windows Setup to find something better, don’t do this. It’s best to obtain a third party driver instead which is actually available.

First, in Dosbox, exit Windows 3.1.

Next, in your regular Windows environment, browse to the folder you’ve been mounting Dosbox to. Create a new folder. I’ll just call this “drivers” to make it easier to remember:

Now, open that directory and create another directory called “s3″. This will be the name of your drivers you are using. If you feel the need to use different drivers in the future, you can simply create another directory in this directory for easy file management:

Now to get the drivers. Thankfully, the folks over on a forum with lots of Dosbox fans have posted the needed drivers (as well as their own tutorial about these and other kinds of drivers). What we are after is the file located in the link I circled below:

Once you have finished downloading the file, open it up and extract all the contents to the s3 folder:

Now, go back to Dosbox. We are going to install these drivers. Simply type in “Setup” and hit enter:

A familiar blue screen should appear. Use the up arrow key to highlight the line next to “Display”. Currently, it is set to the default VGA:

Now, hit enter to go into the video settings. You’ll be able to use your arrow keys to choose which display setting you’ll use. Use the down arrow key and go all the way down to the bottom (holding it down takes you there the fastest). You should find yourself highlighting “Other (Requires disk provided by a hardware manufacturer)”.

This is what we want. Hit enter. You’ll then be taken to this screen:

Now, remember where we put our drivers? Yes, we are working from the mounted folder. If you did exactly what I did when creating these folders, you can simply type in “C:\drivers\s3″:

Hit enter.

After a brief second of loading, you’ll find yourself on the following screen:

Now, you’ll notice that some of these offer something like 64k colours. Since we are talking about 16 bit games, chances are quite good that all we are after is anything in 256 colours (since that is what many are designed to run in). So, you can pretty much pick anything you like here, but try and pick something that ends in either “256 colors SF” or “256 colors LF” (LF is short for Large Font and SF stands for Small Font. I personally chose anything with a small font myself).

You’ll then find yourself on this screen:

Simply press enter at this point. If this is your first time doing this, you’ll be prompted for the directory that the drivers are located again. Simply re-type in the same driver location as before and hit enter. This is only for people who do this the first time. After that, you’ll only ever be prompted to type in the directory once every time you want to change the resolution. If there are any additional screens beyond this, just hit enter until you finally find yourself back at the dos prompt. Type in “win” and hit enter to go back into Windows. You’ll find that the resolution is greatly altered.

You can now freely play many classic 16 bit Windows video games like Mordor smoothly on Windows 7 Home Premium 64 bit!

Questions and Answers

Q: What kind of memory footprint are we looking at for something like this?
A: For me, at the resolution (the second highest at 256 colours SF), my memory footprint while running one game looked like this:

In short, big name browsers with a handful of tabs can take up way more than what you see in Dosbox.

Q: Can something like Windows 95 work on Dosbox?
A: I honestly don’t know how possible that is. One thing to remember is that the newer the operating system, the more memory it will take up to emulate the same game. Chances are good it isn’t really worth it and if it’s newer than the two games I mentioned here, there’s also a possibility that it operates on a 32 bit system which can run on Windows 7. Emulating it via Dosbox would be redundant. In any event, Windows 3.1 is basically a shell program that runs on DOS. Later versions don’t run quite like this, making it much more difficult to emulate (if it’s possible at all).

Q: What about running these programs under WINE in Linux?
A: This is an idea I have toyed with. Unfortunately, the experience of other people seems to suggest that WINE can be buggy. This way, the game is operating in a native Windows environment – an operating system that the games were designed for in the first place.

Q: Couldn’t you just duelboot a different operating system to run these games?
A: That is definitely a possibility. However, I prefer something like this because, this way, no hard drive partitioning would be necessary. You can also run a virtual machine as well. I have no idea what kind of memory footprint is required there, but the process also requires a certain amount of configuration just to get the emulated operating system to run.

Q: Why won’t 16 bit video games run on 64 bit environments?
A: The short answer is that it has to do with coding. We’re talking different pin chips here. There is currently no real way to run a 16 bit video game in a 64 bit environment as the two are incompatible with each other. This emulator theory is about one of the best ways to accomplish playing a 16 bit video game in a 64 bit environment.

Q: Do all 16 bit video games require installing Windows?
A: No. Many 16 bit video games run straight off of DOS. This means you can simply open up Dosbox, mount the C drive and run an executable file to run the game. If a game requires the Windows environment, Dosbox will inform you of this. Both Dare to Dream and Mordor 1.1 require the Windows environment which is why both were demonstrated here.

Q: My game still won’t run! It has errors in it/It says that files are missing!
A: As I suggested in the midst of this tutorial, some games require additional files. Google, in this case, is your friend. You can hope that there is a fan site or even an official website still running that has any additional files required to run the game (like I did with Mordor 1.1). Not every game will run straight out of the box and if you do get any missing files, it can be a case of trial and error to get the game running. Different games have different requirements. The only way to know if a game works is to actually attempt to run it.

Q: Will this work on old general applications too?
A: This should be a great way to try and get general 16 bit Windows applications to run as well. Again, it’s entirely possible to run into similar problems as well (i.e. missing files, etc.) Again, try it out to see if it works.

Q: Where can I get Windows 3.1?
A: There are lots of ways. Look for it. It’s proprietary software, so just linking to it might be legally questionable. Still it isn’t too hard to find.

I hope this guide proves useful for those who are trying to run old applications again. I’ve read about many people being unable to run old applications that require the Windows environment, but are stuck on Windows 7 Home Premium which is why I wrote this guide.

Update

If you find that the game is freezing and you know it normally requires a Floppy drive, try using this guide to get the game running.