From the 1,642-foot summit of this popular peak—which once drew 19th-century literary giants—gaze across the splendor of the Housatonic River Valley.
For almost two centuries, Monument Mountain has been a source of inspiration to poets, novelists, and painters. On August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. It was their first meeting, and, when a thunderstorm forced them to seek refuge in a cave, their lengthy and vigorous discussion inspired powerful ideas for Melville’s new book, Moby-Dick, which he dedicated to Hawthorne. Today, more than 20,000 hikers explore these pale boulders, cliffs, and ledges every year.
Three trails—all under three miles—offer scenic ways for you to get acquainted with the mountain’s pale quartzite geology and wondrous views out to Mount Greylock and the Catskill Mountains.
On the 1.5-mile Indian Monument Trail, you’ll pass the remains of ancient Native American trails, stone walls of former sheep pastures, woods roads, cart paths that brought hemlock bark to tanneries, hearths of charcoal makers, horse-and-carriage pleasure roads, recreational footpaths, and roads traveled by Ford Model T’s. The 0.83-mile Hickey Trail, leaving right (north) from the parking lot, is the most direct—and strenuous—approach. The 0.62-mile Squaw Peak Trail is the summit connector for both the Indian Monument and Hickey trails and offers the best views. Look up to catch hawks and the occasional bald eagle soaring overhead.
Members: FREE. Nonmembers: $5 parking fee.
Fees and Permits
Seasonal hunting is permitted subject to all state and town laws. Learn more about hunting on Trustees reservations.
Great Barrington, MA 01230
From Points East: Mass Turnpike (I-90), Exit 2 to Rt. 20 East. Take 1st right at Rt. 102/Pleasant Street. After approx. 4.6 mi, turn left onto Rt. 7 South and follow for 3 mi.
From Points West: I-90 to Exit B3, NY Rt. 22 South. Take 1st left onto Rt. 102 East. After approx. 8 mi., turn right onto Rt. 7 South and follow for 3 mi. Entrance and parking (56 cars) on right.
From Great Barrington Center: Take Rt. 7 North and follow for 4 mi. to entrance on left.
Free trail map distributed from bulletin board in the parking area. Please understand that supplies periodically run out.
We recommend that you take a photo of the map on your phone so you can refer to it during your visit, or download a trail map before you head out.
Seeking, protecting, and caring for Massachusetts’ most special places
With roughly 27,000 acres under management, The Trustees is devoted to protecting ecologically significant environments across our portfolio.
For almost two centuries, Monument Mountain has been a source of inspiration to poets, novelists, and painters. During William Cullen Bryant’s sojourn in Great Barrington (1815–1825), he penned Monument Mountain, a lyrical poem that tells the story of a Mohican maiden whose forbidden love for her cousin led her to leap to her death from the mountain’s cliffs. In the poem, Mohicans created a rock cairn on the spot where she lay buried, giving the mountain its name – Mountain of the Monument.
We were visiting the Berkshires area for the first time and I came across Monument Mountain as an option for a nice hike. We were not disappointed. We took the gentler ascent from the car park, turning off at the Squaw Peak trail and then came down via the steeper Hickey Trail. The peak trail has some steeper rocky parts along the way but nothing too challenging. The views from the top were lovely.
– GabbaiNo1, TripAdvisor
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