Oregon Trail: 16 bit installation for 32 bit game on 64 bit computer.

Rick_OShay1 · Jul 4, 2017

Very recently, I'd have a wave of nostalgia wash over me, and fill me with a desire to play The Oregon Trail again.

Editions #4 and #5 felt extremely dumbed down, so I insist on playing #3.

My PC is Windows 7 and is 64 bit.
The game is 32-bit, but the installation program is 16 bit, and because of that, the installer insists on not cooperating because it's "incompatible".

P.S. No, I can't change the compatibility until the game itself is actually installed.

The Paladin · Jul 4, 2017

if your installer is on a cd you probably right. the simple solution (and this is a tease of course) is run Linux with a copy of windows 98 on it. then install the game ), but seriously, since I googled it and found this which to me is exactly your issue

"Much older applications that pre-date Windows 95 will sometimes require a bit more work. 16-bit applications, in particular, are not natively supported on 64-bit Windows 10 because the operating system lacks a 16-bit subsystem. This can even affect 32-bit applications that utilize a 16-bit installer."
go visit this web page they seem to have a work around that might help you .
https://www.groovypost.com/howto/enable-16-bit-application-support-windows-10/

James Mason · Jul 4, 2017

You can also just play it on your browser: https://archive.org/details/msdos_Oregon_Trail_The_1990

Rick_OShay1 · Jul 4, 2017

James Mason :

That's Oregon Trail 1, I want to play #3.

Rick_OShay1 · Jul 4, 2017

The Paladin :

Unfortunately, that website is for someone with windows 10, and 10 is radically different than 7.

Plus, I hate vague instructions. And I can't find anyone who gives precise step-by-step instructions.

James Mason · Jul 7, 2017

Hm, well your only option is to install virtual computer software, run a virtual computer, install a 32-bit os (or windows 95 again or whatever) and then install oregon trail 3 and play it on that.

James Mason · Jul 7, 2017

Or you can use DosBox to run/emulate Windows 3.1, which will then let you install oregon trail 3.
http://www.freezenet.ca/guides/compatibility-and-emulation/how-to-play-16-bit-windows-gamesapplications-on-a-64-bit-computer/

Rick_OShay1 · Jul 9, 2017

James Mason :

I am following the link's steps, but hit a snag at step 6. The picture shows a list of folders, whereas on my computer, they are .img, with the iso avatar. The DOS says that it's "an illegal action".

James Mason · Jul 9, 2017

extract them then. ISOs/img files are just containers like .zips and .rars

Rick_OShay1 · Jul 11, 2017

James Mason :

Don't work, they remain .img with the .iso avatar.

James Mason · Jul 11, 2017

You need winrar or another advanced extraction program.

Rick_OShay1 · Jul 12, 2017

James Mason :

I do have, and use, WinRAR.

The files contained within said WinRAR are .img, and have the .iso icon.

And wherever I extract the files to, (i.e. desktop), the files remain as .img with the .iso icon rather than as folders like the step-by-step tutorial shows.

James Mason · Jul 12, 2017

.img files are the same as ISO files, extract them again.
You may have to tell them to open with winrar manually.

Rick_OShay1 · Jul 13, 2017

Ok, I just found out, despite me seeing them on my WinRAR, the iso files are actually 7-zip, hence why WinRAR is stubborn to cooperate.

Is there a way to change 7-zip into actual WinRAR?

James Mason · Jul 13, 2017

maybe, but it'd be easier to just get 7-zip: http://www.7-zip.org/

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