Monument Mountain

Great Barrington, Massachusetts 1230

Monument Mountain

Monument Mountain Professional Guide

Detailed Trail Description from our Guidebook

"For almost two centuries, Monument Mountain has been a source of inspiration for many artists, including poets, novelists, and painters. During William Cullen Bryant’s stay in Great Barrington in the early 1800s, he wrote an expressive poem entitled “Monument Mountain,” which 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. A rock cairn marks the spot where she lies buried, giving the mountain its name—Mountain of the Monument.

With more than 20,000 visitors a year—too many, by some standards—the hike to Squaw Peak is a popular annual ritual. On a beautiful fall day, the 56-spot parking lot often will be brimming with vehicles. To avoid the crowds, you and your dog should visit early in the morning or on weekdays. The summit is spectacular and offers panoramic views of southern Berkshire County."

More Monument Mountain Professional Guides

Detailed Trail Descriptions from Our Guidebooks

100 Classic Hikes in New England (The Mountaineers Books)
Jeffrey Romano
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"Since 1891, The Trustees of Reservations (TTOR)—a more than 100,000-member-strong land conservation organization—has helped to preserve nearly 25,000 acres of Massachusetts’ most special places. In their quest to help each of us to “find our place,” they offer nearly 100 locations for public exploration. One of TTOR’s most popular reserves is the 503-acre parcel that surrounds Monument Mountain’s Squaw Peak."
Best Easy Day Hikes: Berkshires (Falcon Guides)
Jim Bradley
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"Monument Mountain attracts over 20,000 visitors per year and it is no wonder why, given the awe-inspiring 360-degree views of the Taconic Range, Mount Greylock, and the Housatonic River valley. Well-marked trails take you to the summit of Squaw Peak, where you can have a picnic at the summit just like authors Nathaniel Hawthorne and Herman Melville did in 1850. From the map kiosk at the trailhead, head south on the well-marked Indian Monument Trail, traveling the loop in a clockwise direction. The trail follows the edge of US 7 for .5 mile before bending to the right and heading away from the roadway. As you climb Indian Monument Trail, the traffic noise fades. At the junction with Squaw Peak Trail, turn right onto Squaw Peak Trail. The trail to the Squaw Peak summit is steep and rocky in sections but the view is well worth the climb."
AMC's Best Day Hikes in the Berkshires (Appalachian Mountain Club Books)
Rene Laubach
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"It would be daunting to name another hike as steeped in history as Monument Mountain. Some 20,000 hikers annually enjoy a pilgrimage to its fabulously picturesque summit of jagged quartzite boulders capped by pitch pine. Begin at the map kiosk shaded by Depression-era red pines, where trail maps are sometimes available. Visitors are encouraged to support the nonprofit The Trustees of Reservations with a donation. From the kiosk, turn right and head north on blue-blazed Hickey Trail. White pines, black cherries, red maples, red oaks, and white ashes tower above sapling American beech, witch hazel, and striped maples that have smooth greenish trunks. Given that Monument Mountain Reservation was established in 1899, the forest here has had more than 100 years to regenerate. As a result, many white pines and oaks are of impressive proportions."

Monument Mountain Trip Reports

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This hike has great views of the Berkshires from the summit and is mostly easy with a few steep and rocky areas. There's also a lot of bugs so bug spray is a must. Best to go on a weekday, it's a lot less crowded.
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I agree with the two posters below. This is a nice hike but 1) the traffic is a bit distracting and 2) go on a weekday to avoid the crowds. The proximity to Great Barrington is a plus, but do factor in the above caveats.
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I hiked this trail on a beautiful fall morning at the end of October. The hike is short, mostly easy (there are some parts that can be considered moderate), and the views are wonderful as was the foliage. Despite all of these positives this trail had one major drawback, it was incredibly crowded. The crowds really detracted from the experience. The scenic views are from small ledge locations and when you need to wait in line to take a look, it almost makes the hike not worth it.
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This was a nice, short, relaxing day hike. The downside is that for the first part of it you're going along next to the highway which is somewhat out of eyesight due to vegetation, but you still hear the cars whiz by somewhat tainting the experience. Nevertheless, it's a nice hike for how close it is to Great Barrington. The views were nice, though not spectacular. Once one got up to the views, it was nice and quiet, and there were a few great places we found to just sit, take in the view and chat. Very relaxing.

Monument Mountain Photos

Trail Information

Great Barrington
Nearby City
Trail Type
Skill Level
2 hours
Spring through Fall
The Trustees of Reservations
Local Contacts
USGS Great Barrington
Local Maps

Trail Log