Appalachian Trail #2 (US 7 to Upper Goose Pond)

The Appalachian Trail section from Sheffield, Massachusetts to Upper Goose Pond runs through the heart of the southern Berkshires and offers a classic New England hiking experience. Beginning near the Housatonic River valley by Route 7 in Sheffield, the trail gradually climbs away from farmland into mixed hardwood forest, with moderate but steady elevation changes, rocky tread, and occasional roots typical of Massachusetts A.T. hiking. Along the way, hikers pass scenic features such as Benedict Pond, a popular rest and camping spot, and the Tom Leonard and Mt. Wilcox shelters that make this stretch well-suited for a short multi-day backpacking trip rather than a single long day hike.

As the trail continues north, it traverses quiet wooded ridges before reaching the Upper Goose Pond area where there is a cabin with bunk beds, a stove, a dinner table, and a nice deck for lounging in front of the pond. Canoe rentals are also available.  A short blue-blazed side trail leads to Upper Goose Pond itself, a clear, picturesque body of water with swimming opportunities and the backcountry cabin and tent platforms that are seasonally caretaker-maintained. This endpoint provides a peaceful and social stopping place for section hikers and thru-hikers alike, combining natural beauty, reliable camping, and a sense of Appalachian Trail community within a relatively short distance from the trailhead towns.