Bartholomew's Cobble Trail

Bartholomew’s Cobble, located in Sheffield, MA, features a well-marked trail network beginning from a parking area on Weatogue Road. From the lot, head east on Ledges Trail before turning left onto Bailey Trail. At the junction with Tulip Tree Trail, continue straight onto Spero Trail to follow it through open woods and wetland edges, eventually looping back to the same junction. From there, turn left on Tulip Tree Trail, then make another left onto Tractor Path for a steady uphill climb to the top of Hurlburt’s Hill and its sweeping views of the Housatonic River Valley. Descend on Tractor Path and turn left on Hal Borland Trail to return to the parking area through lowland forest and fields. Hikers will find several junctions along the way that allow for shorter return options to the trailhead if needed. Managed by The Trustees of Reservations, this preserve is known for its botanical diversity, including extensive fern populations and one of Massachusetts’ largest cottonwood trees. Trails pass through varied habitats including riverbank forests, fields, small caves, and marshes, providing excellent opportunities for wildlife viewing and nature study. Dogs and other pets are not allowed due to the area’s ecological sensitivity, and a small admission fee applies for non-members. Open year-round, Bartholomew’s Cobble is a standout option for moderate hiking and snowshoeing in the Berkshires.