Appalachian Trail

On the south side of the I-90 Mass Turnpike from Lenox, the other main center of Berkshires cultural life is Stockbridge (pop. 1,947). If Main Street feels familiar, perhaps it’s because the town made its way onto Norman Rockwell canvases during the final decades of his career, when he lived and worked here. You may dismiss his illustrations as the epitome of contrived sentimentality, but only people with hearts of solid flint won’t find themselves grinning after a stroll through the collection of the Norman Rockwell Museum (413/298-4100, daily, $20 adults). The modern museum is on Route 183, 2 mi (3.2 km) west of town. The town itself is well worth a stroll, too, particularly past the grand houses along Main Street that seem frozen in an idyllic past.

While most of the large estate homes around Stockbridge are not open to the public, one of the county’s more extravagant “cottages” is Naumkeag (daily summer, $20 adults), an 1885 mansion on Prospect Hill Road less than a mile north of downtown. The mansion, designed by Stanford White for Joseph Choate, a lawyer who later served as U.S. ambassador to Britain, amply illustrates why this region was regarded as the state’s Gold Coast a century ago. The impressively landscaped grounds are an attraction in their own right.

Sculpture is the highlight of Chesterwood (daily summer, $20 adults), off Route 183 just south of the Norman Rockwell Museum. The residence was the summer home of Daniel Chester French, one of the most popular contributors to the fin de siècle American renaissance. French arrived on the art scene with a bang, sculpting Concord’s Minute Man statue at the age of 23 and 24, but he is best remembered for his statue of the seated president at the Lincoln Memorial in Washington DC. A tour of French’s studio and house (now a property of the National Trust) or a walk around the 122 wooded ac (49 ha) graced with works of contemporary sculptors quickly confirms why French once called his seasonal visits “six months . . . in heaven.”


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. 319). 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 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, which you can follow on a short (3 mi/4.8 km 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.

Great Barrington

While most South County towns have been spruced up like precious antiques, Great Barrington, with as many hardware stores as chic boutiques, is like Grandma’s comfortable old sofa, still too much in daily use to keep under velvet wraps. The town doesn’t deplore the few tacky commercial lots around its fringes, perhaps because they can’t detract from the handsome buildings at its core. Prime among these buildings, which include stone churches on wide Main Street and imposing Searles Castle, a former Berkshire cottage turned private academy, is the landmark Mahaiwe Performing Arts Center (14 Castle St., 413/528-0100), all marble and gilt trim behind its marquee. Built for vaudeville and recently restored, the Mahaiwe still hosts frequent film, theater, and musical theater productions.

Related Travel Guides

Massachusetts Travel Map

Map of Appalachian Trail through Massachusetts.
Map of Appalachian Trail through Massachusetts.