Currently positioned in Michigan. CG Modeller, novice programmer, and overall nice guy.
I need this to happen!
Go to your desktop shortcut and after -overrideBigFile type in this:
Once you add that and run the game you should get an error log in your "~/sierra/bin/release" folder. (it should be called HW2.log) If you find it and post where the error is, I'm sure someone could find an answer for you! ;) Either that, or you could just uninstall and re-install and that might fix your problem.
It's a race that was in one of the early windows 95 game, its so old you needed to started it up in DOS, it was still actually pretty cool ;)