I have a Rakefile that I wrote to simplify deployment of Rails apps on Windows. It's provides similar tasks to Capistrano, but runs on the target server, not by executing remote commands via ssh - as such it's only really suitable for single server deployments. Let me know if you'd find this useful and I'll send it to you.
cheers, Ben
I hate to admit it. But I ended up using Ant to zip up everything and just unzip it on the target windows development server. Then I restart Mongrel and Apache. Total time for delivery...about 80 seconds.
KISS principle. Yeah I could Capistrano...except my company has a very involved software delivery process and uses CVS and not SVN. So this was the simplest approach. Works like a charm in my dev test servers. (Though I did freeze my Rails version to make my life simpler.)