I'm not sure why it is, but Colorado Springs has a very nice collection of classic cars. It is not at all uncommon when driving around on a weekend to see a beautifully restored 1957 Chevy, or a 1950 Studebaker, or a 1968 VW Bus, or any of a number of other cars that collectors love. I know a fellow who has an authentic, perfectly restored 1965 Shelby Mustang.
I'm not talking about old beaters that some working man couldn't upgrade. They are collectors' cars, usually with beautiful paint jobs and occasionally tricked out with fancy engines and the like.
I can't guarantee that it you are here for a week or two, that you will see any classic cars. But I see them all the time, and you might get lucky.