Route 8, US-20, and the Mass Turnpike all cross the Appalachian Trail at Greenwater Pond east of Lee, but a much more scenic stretch of the trail can be accessed south of here in the village of Tyringham (pop. 420). Site of a Shaker community in the 1800s, and later a popular artist colony, this small hamlet is situated in a delightfully rural landscape of small farms and rolling pastures. The main sight here is an odd one: Santarella (413/243-2819) the hand-hewn home and studio of British sculptor Sir Henry Kitson, whose many works include the Pilgrim Maiden monument at Plymouth and the Minuteman at Lexington Green. His house is a place where Bilbo Baggins of The Hobbit would feel at home, with its sculpted rocks, twisting beams, and organic-looking, pseudo-thatched roof. Although it’s not open for tours, you can stay overnight at its cottages. It is also available for events.
South of Santarella, beyond the ever-quaint center of Tyringham, a signed parking area marks the crossing of the Appalachian Trail, which you can follow on a short (three-mile round-trip) hike through fields of wildflowers up through Tyringham Cobble to a ridge giving a good view over this pastoral valley, which feels far more remote than it really is.