Massachusetts

Stockbridge: Norman Rockwell Museum (the Four Freedoms!), Chesterwood, Stockbridge Bowl (pretty), Monument Mountain
Lenox: Tanglewood, summer home of the Boston Symphony Orchestra (although I doubt the grounds are open now - if they are it's lovely), The Mount (also probably closed)
Mt. Greylock: nice to hike, recreate a hike that Thoreau described in "A Week on the Concord and Merrimack Rivers". Emerson also hiked it e.g., The Unpardonable Sin, Ethan Brand
Arrowhead: Melville's home
North Adams: Massachusetts Museum of Contemporary Art
Northampton: Hang out

Feel free to PM with any questions. I'm a Bostonian (technically a Newtonian) but have spent a good bit of time in western MA.