Near Lenox, the Metacomet-Monadnock Trail is a 117 mile foot path from Connecticut to Mt. Monadnock in New Hampshire. It is maintained by the Berkshire chapter of the Appalachian Mountain club and other volunteers. The trail follows a corridor of elevated wildland from the basalt ridges of northern Connecticut clear through central Massachusetts to a dramatic finale on the craggy summit of 3,113-foot Mt. Monadnock. It beguiles with quiet rivers and mysterious hemlock ravines, then hurls you onto wind-buffeted, sun-seared mountain balds with Panavision views. Southern portions of the route, especially along the Mt. Tom and Holyoke ranges and the Pelham Hills, are reminiscent of English country walking: You hike a densely wooded ridge punctuated with spill-away vistas of pastoral beauty to each side. In northern Massachusetts, the M&M becomes a wilderness trail, a guise it maintains as the mountains grow taller and road crossings become less frequent.
Overall, Metacomet-Monadnock Trail is the 17th most popular hiking trail of all 36 hikes in Massachusetts.