Odd how so many of the old valued customers who want to do this have a history of less than 10 posts...
 
Regardless - the least painful way to run 16 bit software (Windows or DOS) on a modern machine is to slap a 32 bit OS on it. Otherwise you're talking about setting up a virtual machine.
 

Wow!!!!  Thankyou Paultomasi.
What a great informative tutorial.
Can't wait to try these tips out.
I am on Win7 64 bit.
I have a friend who gave me a thumb drive version of CPW30 he had copied from an old machine
running XP.   Somehow it works and I have been happily editing my Rep all day in my fave MIDI prg on an Acer netbook running win7 32 bit starter.
This has not been possible for 15 years.
Still have original Floppy disk which i paid $500 for in '94 in Australia - and it spins up in a USB floppy drive but won't install on win 7.  However, my friends version on thumb drive DOES...WooHoo

I must, even now, YEARS later, add my voice to the fans of the CWP3.0 sequencer software design and workflow!   
 
Cakewalk made a big mistake when they decided to integrate the process of sequencing midi tracks into what is primarily an audio processing environment. The two processes are entirely and fundamentally different! 
 
Sure you need to have some processing in the Midi/audio environment to 'fine-tune" your midi tracks (in a single environment)...but for me the fundamental elements of sequencing midi (which often involved cutting and pasting blocks of repetitive data) is simply impossible in the new products.
 
Give me CPW 3.0 anyday! 
 
It is the workflow of 3.0 that was so well designed and easy to use (unlike the products that have 'mixed' audio and software) As a composer / muso its sequencing facilities were and are ground-breaking, even 20 years later. 
 
But sadly it is rapidly approching extinction, as new operating systems, sound modules,, virtual instuments and and controllers follow the "New" and "Better" ways dictated by the "audio" clan (who prefer to just slap together someone elses "loops" and clips rather than write music from scratch.. 
 
I would gladly support a dedicted sequencer product so I can continue to create my 'own' music.
 
Just saying! 
 

You could always try a virtual machine OS workaround however you still need to access your sound drivers through another interface. So bare in mind, there will be added latency.
 

artmat
I've been a Cakewalk user since the time 12-Tone Systems had only a 1-horse engine. I still have my original 5-1/2 inch floppy installation disk. I currently use Cakewalk 3.01 with Windows XP-Pro in a big way and for me, it runs perfectly fine on that OS.
 
I'd love to see the company make an effort to address the requests of many of its loyal long-term users by updating the original CW3.01 so that it operates on Win7-64/32 and Win8 while keeping its original design and layout in tact as much as possible. (I love the dots....  etc) My Cakewalk 9 Pro Audio works fine on Win7-64 but CW3.01 is still my favorite program and I dearly miss having it on my Win7-64 machine. 
 
I'd also be very happy to pay a reasonable price for an updated version of the old CW3.01 that works on Win7-64.
 
ArtMat

Hi ArtMat,
Ive been looking around for a xp pro laptop to run my 3.01 cakewalk. Do you know if it works on just Xp home edition as well. Are you using the parallel port or a usb midi interface
regards
Kaffmate
 

Does anyone know of any software that'll read and convert Cakewalk wrk. files to midi files? I have so many wrk. files from Cakewalk 3.0 or 3.1 and I desperately need a way to open them and re-save them as midi files. Help please!!!

Wouldn't any version of Pro Audio or SONAR open a cakewalk.wrk project file? It's been years since I've done it, but I'm certain I've opened early Pro Audio projects and reworked them in SONAR. Of course it doesn't work the other way around, but never had any "upward" compatibility problems ever, save for no longer having/using the plugins and or MIDI instruments.