Ogden Gigli/Courtesy of 1Berkshire

Key Info

545 Stockbridge Rd

Price & Hours



Free, Hiking, Sightseeing 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.

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#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.

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