Here is an example of a Perl/Tk app I wrote, which runs on Windows under active perl: http://www.lightandmatter.com/ogr/ogr.html The pdf file containing the documentation gives (possibly out of date) instructions for installing it on Windows, on p. 2. The install_win.pl script packaged with the software installs the necessary activestate modules for the user.

That system worked okay, but it was kind of a pain. I've had my eyes peeled to see if anything better would come along for Windows users, but haven't found it yet. Here are some people's comments on versions of perl for Windows: http://stackoverflow.com/feeds/question/71513

I would suggest trying both strawberry perl and activestate and seeing which one suits your needs better.