Spring Street is the main street in Williamstown, with all of the Berkshire charm. You can start near Williams College's campus, and walk down past the deli (where sandwiches are named after the famous actors who've performed at Williamstown Theater Festival), yoga studios, clothing stores, and plenty of warm restaurants and bars. Tunnel City Coffee is a must in our book, as is Lickety Split for ice cream. There's also a tiny independent movie theater, where Phil has killed many hours waiting for Michael to finish his shift at the theater festival.
Fun fact: this is the mountain Phil grew up skiing at, and where we've spent so many winter weekends. We can't say enough about this mountain, specifically the variety of trails for all levels, the great ski school, and the beer at John Harvard's. Ski or snowboard Saturday morning, or join the happy couple for first tracks as husband and wife on Sunday afternoon.