Summer Outdoor Activities in South Berkshire County Massachusetts

With a cornucopia of choices for family adventure activities near New York City, the Berkshires of western Massachusetts are an ideal summer destination. South Berkshire County combines outdoor arts venues such as the iconic Tanglewood Festival (summer home of the Boston Symphony Orchestra) with hiking the Appalachian Trail, visiting the Norman Rockwell Museum, paddling the Housatonic River, watching a play at Shakespeare and Company, ziplining at Catamount's Aerial Adventure Park, or buying food at the Berkshire farmers' markets.

Located just over a two-hour drive from New York and the tri-state metropolitan area of New York, New Jersey, and Connecticut, "South County" is the part of Berkshire County south of Interstate 90. The most popular outdoor activities include hiking, backpacking, paddling, swimming, biking, and ziplining,.

Hiking and Backpacking in South Berkshire County

The Appalachian Trail runs straight up the line of the Berkshires from the Connecticut border to Vermont. The trail in South County starts just north of Sage's Ravine, between Salisbury, Connecticut, and Sheffield, Massachusetts. One of the highlight hikes is to tackle the climb of Jug End, which begins at a small trailhead on the Jug End Road in South Egremont, and and rises steeply above the Housatonic Valley. Wild blueberries are the reward for a steep rocky scramble.


Monument Mountain offers a short, stiff climb to a spectacular view point over Stockbridge (home of the Norman Rockwell Museum, the famous Red Lion Inn, and the former Alice's Restaurant of Arlo Guthrie fame) and the Housatonic River Valley. For the first half-mile of this walk, hikers might curse the noisy traffic on Route 7, but after that falls away, the trail ascends quietly.

Monument Mountain has some interesting history: the Indian Monument that gave it its name, and its local fame as a place where Herman Melville and Nathaniel Hawthorne met and hiked together. The top features lots of craggy boulders that make excellent picnic spots with a sweeping view. The nearby Ice Glen hike, also boulder-strewn, is another local favorite, with a viewpoint as a reward..

Bicycling in the Berkshires

Road biking is popular in Berkshire County. Cyclists will find that the back roads are much safer than State Highways, especially routes 7, 23. and 41, which are the busiest. Some of the back roads, however, turn to dirt, so either check the route carefully or bring a hybrid bike that can handle the bumps. For hybrids and mountain bikes, the Mt. Washington Road is a fantastic ride in late June, when the mountain laurel are in bloom. Cyclists who are up for it can start from the town of South Egremont, but it's a solid thousand feet to the top: Those not up for the climb can start in the tiny hamlet of Mt. Washington.

There's a bike shop (Berkshire Bike and Board) in Great Barrington, and a bicycle outfitter (Bash Bish Bicycle) in nearby Copake, New York, situated just at the Massachusetts border, close to Bash-Bish Falls, the Taconic State Park campground, the South Taconic Hiking Trail, and the Harlem Valley Bike Path.

New in 2009 was a mountain bike course at the Catamount Ski area, where on weekends, ski lifts especially outfitted with bike carriers whisk cyclists to the top, and a network of trails leads back down. There's also a training course at the bottom for newcomers to the sport of mountain biking.

Paddling and Swimming in Berkshire County

The Housatonic has some nice stretches for kayakers. The Arcadian Shop, on Route 7 in Lenox, offers equipment and organized trips. Swimming lakes and holes abound, although permission to park is sometimes restricted to those with town stickers. However, two of the best sites are free, and open to everyone:

The Green River is the local favorite "secret" swimming and fishing hole, but it is not such a big secret; the dozen or more cars parked on the side of the road over the Green River bridge on Routes 41/23 betray its location. The Green River swimming hole is found on Routes 23 and 41, about 1.5 miles west of the junction with Route 7 in Great Barrington. After parking, follow the trail downstream (south) on the east side of the river. Watch out for poison ivy on the trail.

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Lake Mansfield is beloved by local families and visitors. Cooperatively manged by the National Park Service and the town of Great Barrington, it's open to all (no local stickers required). The lake is a tiny jewel with a swimming area, a small beach, a picnic area, and some grass for playing. There's also a boat ramp for kayaks, canoes, rowboats, and small sailboats.

Finally, other major South County attractions include North America's largest aerial adventure park at the Catamount Ski Arrea, Bash Bish Falls (which is the highest waterfall in Massachusetts), and a riverside path along the Housatonic River in Great Barrington, just off of Main Street. The outdoor season extends from May through the late October foliage season. But it only takes one weekend visit for tourists to understand why the region has become such a favorite for tourists, second-home owners, and weekenders.

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