Definitely go check out his museum in Stockbridge, MA... its fantastic. Also check out Joe's Diner on Main St in Lee (exit 2 off the pike, where you'll probably get off anyway). This is where he painted the famous shot of the officer glanding down at the young kid next to him on the diner stools. It's still exactly the same at Joe's.
I grew up in the town next door, Lenox. The Berkshires in general are a wonderful place for wide range of photog - nature & birding (some bald eagles have returned the last few years), landscapes, lakes, but also live music at Tanglewood & Club Helsinki, theater and fine art (NR museum and MOMA in N Adams).
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