Flag Rock Trailhead
Monument Mountain Reservation
Great Barrington, MA
Snowshoeing | Hiking | Climbing
The Monument Mountain Reservation is a stunning area within Western Massachusetts that allows visitors to hike up and around one of the most striking mountains in the Berkshires. Monument Mountain rises above the rest of its mountain range, given that it is tall but capped with a steep rock face. The Hickey Trail is one of the best, most efficient ways to climb this face, as it is less than a mile long but travels to the top of the mountain. It is a very steep trail, often supplemented by steep stone steps and sometimes just a steep dirt path. Although it is a challenge, the scenery on the trail is stunning. It passes through Monument Mountain's dense, beautiful forests, where various animals live and mushrooms grow. It goes along the rim of a steep gorge where a stream has carved its path for years, and it even has an easy access point to a waterfall, where hikers can get right up close to the cool, cascading water.
At the peak, hikers can switch to the Peeskawso Peak trail, which travels along the rock face on top of the mountain and enjoy the stunning views of the valley below. The Peeskawso trail leads to Devil's Pulpit, another pristine valley vista with a fascinating rock structure. Monument Mountain is a fantastic location for visitors to the Berkshires and a hiking destination nobody should miss.
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Parking for Monument Mountain Reservation can be found directly off Route 7. At least 20 parking spots can be found over compact, level gravel. An additional 10 spots are located over a flat, grassy area adjacent to the gravel path. Parking is metered, with a $6 fee. A small picnic area containing multiple wooden picnic tables rests in front of the parking area, between the two trail entrances to the reservation. Two trails branch off from the parking area: the Hickey trail and the Mohican Monument trail. The .9-mile Hickey trail consists of dirt, containing sections of roots throughout. Additionally, the Hickey trail contains consistent grades of 15-20%, with maximum grades approaching 25%. The 1.6-mile Mohican Monument trail, also comprised of dirt, starts flat before climbing to sustained grades of 10-15%, with maximum grades approaching 20%. Multiple sections of roots and rocks are present throughout the trail. The Peeskawso Peak trail connects to both trails and offers access to the Devils Pulpit, contains moderate grades, with narrow sections and moderate rock scrambling.
Looking to meet up with others for team sports or group activities? Check out our list of clubs, guides and leagues in the Berkshires on the Resources page. Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.
We also link to an array of outdoor recreation retail shops for gear and rental facilities for equipment on the Gear page.