Monument Mountain
Great Barrington, MA
503 acres
Bird Watching Cross-country skiing/Snowshoeing Hunting Mountain Biking Not Permitted Walking/Hiking (Strenuous) Picnicking

About Monument Mountain

Ascend this popular peak, which once drew 19th-century literary giants, and from its summit gaze across the spectacular landscapes of the Housatonic River Valley.

What makes Monument Mountain a Special Place?
We think it’s the memorable views of the southern Berkshires and the broad Housatonic River Valley awaiting you from the summit. For two centuries, this imposing natural feature has attracted artists and writers, hikers and nature lovers. Each year, more than 20,000 visitors explore Squaw Peak, descending with memories they can share for a lifetime.

But Monument Mountain isn’t exceptional just for its spectacular scenery. Its geology is just as remarkable: the mountain is composed predominantly of pale quartzite, rising abruptly above the Housatonic wetlands and river valley.

From the 1,642-foot summit of Squaw Peak, you’ll enjoy views as far north as Mount Greylock, near the Vermont border, and, in the western distance, the Catskills of New York. Hawks (and even the occasional bald eagle) soar gracefully above the serene Housatonic River Valley spreading below. 

Remember, you’ll be “earning” the spectacular views offered from the higher reaches and summit, so a basic level of fitness is required to handle the 720-foot elevation gain. Wear sturdy shoes and bring plenty of water. Understand that wet weather can make for some slippery footing. Be especially cautious on the ledges; keep an eye on children and pets.

The trails offer several “loop” options, none longer than three miles.

  • The 1.51-mile Indian Monument Trail brings hikers past more than 300 years of history – 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 foot paths, 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

When to Visit
Year-round, daily, sunrise to sunset. Allow a minimum of 2 hours. Caution: Steep routes, ledges, and peak can be dangerous when icy. Please note that the parking lot is not plowed in winter.

Picnic tables

Regulations & Advisories

  • Dogs must be kept on a leash at all times.

  • Some trails are steep and conditions may vary depending on the weather and season. Take caution on summit ledges, especially in winter.

  • Please stay on marked trails to prevent soil erosion.

  • A basic level of fitness is required to hike to Squaw Peak.

  • Rock climbing is prohibited.

  • Fires are prohibited.

  • Seasonal hunting is permitted subject to all state and town laws. Learn more about hunting on Trustees reservations.

The Trustees reserves the right to photograph or video visitors and program participants for promotional use, and usage of our properties implies consent. Find the full policy here.


Route 7
Great Barrington, MA 01230
Telephone: 413.298.3239

Latitude: 42.2431
Longitude: -73.3352

Get directions on Google Maps.

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.


When to Visit
Year-round, daily, sunrise to sunset. Allow a minimum of 2 hours. Caution: Steep routes, ledges, and peak are dangerous when icy. Please note that the parking lot is not plowed in winter.

Members: FREE. Nonmembers: $5 parking fee. Get more information about parking fees >>

Fees and Permits
Seasonal hunting is permitted subject to all state and town laws. Learn more about hunting on Trustees reservations.

Property History

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.

On August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. A thunderstorm forced them to seek refuge in a cave where a lengthy and vigorous discussion ensued, inspiring powerful ideas for Melville’s new book, Moby Dick, which he dedicated to Hawthorne.

You wouldn’t think it today, but this forest was once wiped out, to supply fuel to several iron furnaces in the valley. Coal bush workers lived on the mountain months at a time, tending their hearths. Flattened circular mounds scattered all over the mountain are a reminder of their labors. Often a birch tree grows near them to signal slow restoration of the soils.

Property Acquisition History
Original acreage a gift, with endowment, of Miss Helen C. Butler in 1899. Additional land given by John Butler Swann in 1980. Additional land purchased in 1985 and 1986.

Maps and Resources

Printed trail maps are distributed free from bulletin boards in parking areas. Please understand that supplies sometimes run out. We recommend that you download a trail map before you visit.

Planning Your Visit

Before You Go
We encourage you to visit as many Trustees properties as you can.

Wherever your travels take you, please observe all posted regulations, follow special instructions from property staff, and keep in mind the Stewardship Code:

  • Protect wildlife and plants.
  • Guard against all risk of fire.
  • Help keep air and water clean.
  • Carry out what you carry in.
  • Use marked footpaths and bridle paths.
  • Leave livestock, crops, and machinery alone.
  • Respect the privacy of neighboring land.
  • Enjoy and share the landscape with others.

Click on links below for further visitor information:

Before Setting Out

Enjoying Trustees Reservations


About Hunting on Trustees of Reservations Land

Tell Us What You Think

We’d love to hear about your visit! Here are three easy ways to let us know what you think:

  1. Take our visitor survey. If you have a question for us, you can ask us in the survey and we’ll get back to you.

  2. Post a comment about your visit on our Facebook page.

  3. Share your experiences with other visitors on our website. Simply fill out the form below, and we’ll post your comment right here on this page.

Submitted by MSquare on: June 14, 2014
Just did this hike with my daughter, went up Indian Monument Trail until it connected with Squaw Peak Trail, at the top there are nice views. Then returned by Hickory Trail, which travels along a creek and a couple little water falls. Lots of big boulders at top of Squaw Peak and starting back down but nothing a somewhat out of shape 61 yr old grandma couldn't handle.

Submitted by joezeff on: November 8, 2011
at devils pulpit did one of the rock towers fall? ps i got lost!!!!

Submitted by The Trustees on: April 26, 2011
Dear RRK, The Indian Monument Trail is 1.51 miles from the parking lot to Inscription Rock at the northern end of the Squaw Peak Trail. It does not loop back. The entire round-trip hike is about 3.2 miles. Have fun!

Submitted by RRK on: April 18, 2011
Hi, I'm planning on visiting Monument Mountain with my kids in June, and would like to know whether the Indian Monument Trail loops back to the beginning? How long is the entire, "round-trip" hike: 1.51 miles, or twice that? Thanks very much for your help.

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