Monument Mountain

#3 in Best Things To Do in The Berkshires
Monument Mountain picture
Ogden Gigli/Courtesy of 1Berkshire

Key Info

545 Stockbridge Rd

Price & Hours



Hiking, Sightseeing, Free Type
2 hours to Half Day Time to Spend


  • 5.0Value
  • 3.5Facilities
  • 5.0Atmosphere

Follow in the footsteps of literary legends Herman Melville, Nathaniel Hawthorne and Oliver Wendell Holmes with a hike up Monument Mountain. Calling the town of Great Barrington home, Monument Mountain brims with history and striking views that overlook the Housatonic River Valley and Mount Greylock. Come prepared with your walking shoes and water – it takes some endurance to tackle the 720-foot elevation gain on the way up to Monument Mountain's 1,642-foot Squaw Peak.

Outdoor enthusiasts who visit the Berkshires will appreciate the mountain's various trails, which range in difficulty. If you're looking for a leisurely climb up, take the Indian Monument Trail – a 1 1/2-mile path that climbs the west face of the mountain. For the most direct route, take the Hickory Trail, which measures less than a mile, but is considered the most strenuous. As you make your ascent, heed the advice of recent visitors and take in these views with a mid-hike picnic.

Monument Mountain is accessible year-round from sunrise to sunset. It is recommended you set aside at least two hours to hike to the summit. Parking is available for a $5 fee. There are no bathroom facilities or concessions, but visitors can bring food and drinks to enjoy at the on-site picnic tables or on top of the mountain. For more information on the different trails, check the Trustees of Reservations preserve website.

More Best Things To Do in The Berkshires

Tanglewood1 of 14
Jacob's Pillow2 of 14
Time to Spend
#1 Tanglewood

The summer home of the Boston Symphony Orchestra, this open-air music venue attracts thousands of visitors who come to enjoy a variety of classical, contemporary, jazz and pop music performances every year. The Boston Symphony Orchestra has spent its summers at this grand estate located between the towns of Lenox and Stockbridge since 1937. Over this time, many renowned artists have also made appearances at the venue, including Yo-Yo Ma, Earth, Wind & Fire and Steely Dan. Tanglewood is most popular during the summer when the weather allows for sitting on the property's large lawn during performances. Still, the grounds also house multiple indoor facilities and restaurants, which enable visitors to enjoy programs, galas, events and cocerts year-round.

Reviewers call Tanglewood a "music lover's paradise," with charming scenery that keeps travelers returning year after year. Visitors appreciated the well-manicured grounds and world-class concerts, but recommend bringing your own lawn chairs, food and drinks to avoid the hefty prices of concession trucks, restaurants and stores on the property. Whether you bring your seating or rent from the facility, friendly staff can help you get situated, according to reviewers.

Read more
Chamberednautilus/Wikimedia Commons
See full list of Best Things To Do in The Berkshires »

Explore More of The Berkshires

If you make a purchase from our site, we may earn a commission. This does not affect the quality or independence of our editorial content.


The 50 Most Beautiful Places in the World

Let these gorgeous destinations inspire you to travel more.

Holly JohnsonJanuary 16, 2020

50 Amazing Honeymoon Ideas

From relaxing weekend getaways to epic adventures, these honeymoon trips will help couples create memories to last a lifetime.

Kyle McCarthyJanuary 8, 2020

The Cheapest Days to Fly: A Guide to the Best (and Worst) Times to Travel

Use these tips and tricks to get the best deal on your next flight.

Lyn MettlerDecember 23, 2019

30 Top Florida Weekend Getaways

Spend sun-filled days exploring Florida's beautiful beaches, cities, parks and small towns.

Gwen PratesiDecember 9, 2019

The Best Travel Backpacks for 2020

U.S. News rated the best travel backpacks using recommendations from experts and consumers.

Lyn MettlerNovember 25, 2019

30 Top Wellness Retreats

Rejuvenate your mind, body and spirit at one of these relaxation-focused properties.

Kyle McCarthyNovember 21, 2019

30 Fun All-Inclusive Family Vacations

Book one of these all-inclusive trips that cover food, accommodations and activities galore.

Holly JohnsonNovember 14, 2019

5 Ways Cruise Lines Are Becoming More Environmentally Friendly

Industry considers impact as it looks to the future.

Gwen PratesiNovember 12, 2019

11 Unique and Quirky Cruise Destinations

Venture off the beaten path for an authentic cruising experience.

Christine SmithNovember 12, 2019

The 2020 Best Cruise Lines for Families

Gather up the gang and head out to sea with one of these six kid-friendly cruise lines.

Nicola WoodNovember 12, 2019