Monument Mountain summit panorama

The view from the top – “Monument Mountain panorama” by Tom Walsh is licensed under CC BY-SA 3.0

Looking for something spectacular to do during your Berkshires getaway? Try a hike to the summit of Squaw Peak on Great Barrington’s Monument Mountain Reservation for panoramic views of the Housatonic River Valley and beyond.

Best of all?

The trailhead is just a little over ten minutes from our Berkshires bed and breakfast, Applegate Inn.

Monument Mountain is a unique, 2.5 mile (4.0 km) long ridge of erosion resistant, pale quartzite located in Great Barrington and Stockbridge, MA. Its imposing profile in the Berkshires landscape has long drawn a wide variety of visitors. Some quite famous!

William Cullen Bryant wrote about it in his 1815 “Monument Mountain” story. Nathaniel Hawthorne and Herman Melville, caught by a storm on the mountain, hunkered down in a cave and engaged in a discussion that would help inspire portions of Melville’s “Moby Dick” novel.

Monument Mountain summit

On a clear day, you can see for miles from the summit
“Monument Mountain” by Tom Walsh is licensed under CC BY-SA 3.0

The ridgeline has several distinct peaks, the highest of which climbs 1,739 feet (530 m). The only official trails on the mountain, however, ascend Squaw Peak. This knife-edged summit on the southeast side of the mountain reaches 1,642 feet (500 m) in elevation. It is part of the 503-acre (204 ha) Monument Mountain Reservation managed by The Trustees.

Hiking the Mountain

The Monument Mountain Reservation trailhead parking lot is located on Massachusetts Route 7, north of Great Barrington center.

There are three loop trails one can hike at the Reservation. The combined loop, rated as moderately difficult, is just under three miles (4.83 km) in length. Be sure to pick up a trail map at the trailhead.

Indian Monument Trail is 1.51 miles (2.43 km) long. It passes by ancient Native American trails, stone walls, charcoal hearths, and old, long-abandoned roads.

Hickey Trail, a steeper .83-miles (1.34 km), leaves directly from the parking lot and features an unnamed waterfall.

The .62-mile (.99 km) Squaw Peak Trail connects to both trails and, as the name implies, takes you to the summit. The 720-foot (219 m) elevation gain to the top provides a nice workout with one heck of a payoff.

Devils Pulpit on Monument Mountain

“Devil’s Pulpit” by Mwanner is licensed under CC BY-SA 4.0

Views from Squaw Peak include the Housatonic River Valley, the Berkshires, the Taconic Mountains, and the Catskill Mountains of New York.

You’ll also be able to catch a sight of The Devil’s Pulpit, a large, free-standing pillar of stone below the peak. Wildlife fans: keep your eyes peeled for hawks and bald eagles. So beautiful.

Monument Mountain Reservation

The reservation is open year-round, sunrise to sunset, for hiking, picnicking, bird watching, and hunting (in season). There is a $5 parking fee for non-members.

Visit for more information.