I did a quick search and came across Chocolatey. There may be other package managers for Windows that might do the job. I'm not 100% clear on what Cygwin needs to do to integrate itself with Windows, and how dependent that is on the Windows version, but it might work. You are also getting access to a package manager, which Windows is lacking and which will allow you to install tor and then help you keep it up-to-date. What Cygwin does is to create an overlay that allows linux to talk to Windows. First, you might install Cygwin, putting the root directory on your USB. Since it's Windows (you might have made that clearer in your question), there are two approaches I'd try. If you were using Linux or OSX, I would try using the Homebrew package manager, with its root on your USB.
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