The VSCCA (Vintage Sports Car Club of America) is turning 50 this year, and they are hosting a rally (well, it's really a tour -- so don't worry about your car keeping up). It's an open event. You don't have to be a VSCCA club member, and your car doesn't have to be a VSCCA-eligible car. Although it's probably more fun to enter with a sports car, or at least a vintage car. (Minicars are, of course, welcome.)
The tour starts at the Red Lion Inn, in Stockbridge, Massachusetts. From Friday evening (June 20th) through Sunday, tour participants will travel through the Berkshires, taking in the sites, and eating at really wonderful restaurants.
Details on the tour can be found at: VSCCA 5oth Anniversary June Tour.