The Berkshires Travel Guide

USA  #7 in Best Weekend Getaways in New England
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Best Things To Do in The Berkshires

The Berkshires region of western Massachusetts is known for its outdoor adventures like hiking and water sports, as well as cultural experiences. Home to several performance centers, including Tanglewood and Jacob's Pillow, the Berkshires offers a variety of shows and events year-round. What's more, there are also a plethora of museums that reel in history buffs and art lovers, including the Norman Rockwell Museum and "Moby Dick" author Herman Melville's Arrowhead Home

How we rank Things to Do

Updated September 6, 2019

  • #1
    Things to do in The Berkshires
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    #1 in The Berkshires
    Entertainment and Nightlife, Festivals
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Entertainment and Nightlife, Festivals
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

  • #2
    Jacob's Pillow
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    #2 in The Berkshires
    Entertainment and Nightlife, Festivals
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Entertainment and Nightlife, Festivals
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    Follow the sounds of dancing feet to the Berkshires' 225-acre National Historic Landmark, Jacob's Pillow. A recipient of the National Medal of Arts, Jacob's Pillow is home to one of the most renowned dance training centers in the nation as well as the longest-running international dance festival. The festival, which takes place from mid-June to the end of August, hosts more than 50 dance companies and 500 free performances, talks and events.

    Audiences love watching performances with the backdrop of the picturesque Berkshires. Reviewers appreciate the pre-show talks that explain the upcoming performances' background and meaning. What's more, visitors are permitted to bring their own picnics and wine to avoid the expensive prices at the on-site restaurants. However, visitors who indulged in a meal at the property's Old Inn On The Green say it is worthwhile.

  • #3
    Monument Mountain
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    #3 in The Berkshires
    Hiking, Sightseeing, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Hiking, Sightseeing, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

  • #4
    Mount Greylock
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    #4 in The Berkshires
    Hiking, Monuments and Memorials, Recreation, Sightseeing
    TYPE
    Half Day to Full Day
    TIME TO SPEND
    Hiking, Monuments and Memorials, Recreation, Sightseeing
    TYPE
    Half Day to Full Day
    TIME TO SPEND

    Mount Greylock boasts the highest point in the state of Massachusetts. Located in the town of Adams, its summit reaches 3,491 feet. On a clear day, visitors to the summit can see as far as 90 miles. The area offers a variety of seasonal activities, including hiking, camping, hunting, snowmobiling, skiing and educational programs led by local park rangers.

    Recent travelers said Mount Greylock is a great excursion because it caters to hikers of all levels thanks to a variety of trails. Helpful and friendly recommendations by the rangers at the visitor center were also appreciated and added to the quality of hikers' experiences. Reviewers agree that the views are worthwhile, whether you're taking the scenic driving route or tackling one of the many hiking trails. At the peak, travelers appreciated the touching Veterans War Memorial Tower and a meal at the Bascom Lodge. Past visitors recommend making a reservation to avoid waiting once arriving at Mount Greylock's summit for a sunset dinner.

  • #5
    Clark Art Institute
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    #5 in The Berkshires
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    The Sterling and Francine Clark Art Institute in Williamstown displays exhibits featuring collections of European and American paintings, sculptures, drawings, photographs and other unique forms of art ranging from the Renaissance to the early 20th century. You can observe masterpieces throughout the museum on your own or download a multimedia guide to your smartphone (for an extra fee) to virtually walk you through exhibitions. Outside the museum, you'll find picnic tables and nature trails.

    Recent visitors expressed excitement about the wide range of world-class displays within the museum. They also suggested picnicking by the reflecting pool followed by a scenic stroll on the campus trails outside the Clark. Reviewers also appreciated that the museum offers something for everyone thanks to its diverse and ever-changing exhibits.

  • #6
    The Mount
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    #6 in The Berkshires
    Historic Homes/Mansions, Tours
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Historic Homes/Mansions, Tours
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    Once the home of author and humanitarian Edith Wharton, this Lenox estate includes a 42-room country house and formal gardens that span nearly 50 acres. Wharton's home and gardens teem with stories of her vibrant life, philanthropic work and literary legacy. House and garden tours offer visitors a glimpse into the author's past, while the seasonal "Backstairs" tour provides a behind-the-scenes look at the servants who lived at The Mount. Ghost tours are also available from July to October. Visitors at The Mount will also find a terrace cafe, a bookstore, forest hiking trails and a cultural center, which plays host to a variety of community events.

    Visitors applaud the entertaining and informative guides, who they say bring Wharton to life. Reviewers suggest setting aside several hours to tour the property and gardens, as you'll want to take your time admiring the estate.  

  • #7
    Pleasant Valley Wildlife Sanctuary
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    #7 in The Berkshires
    Hiking, Sightseeing
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Hiking, Sightseeing
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    Located in the town of Lenox, this 1,211-acre wildlife sanctuary run by the Massachusetts Audubon Society features 7 miles of trails, a large pond, and striking views of forest, meadows, wetlands and wildlife. There are many well-marked walking trails to explore, which range in length and difficulty. The All Persons Trail fits its title as a mostly flat and 30- to 40-minute easy loop around Pike's Pond where hikers can often spot beavers. For the more adventurous, the Trail of the Ledges is a 3-mile loop that challenges visitors to hike a steep vertical to the top of Lenox Mountain, which reaches an elevation of 2,126 feet. The strenuous hike up is well worth the vistas of Mount Greylock, the Taconic Range and the Catskill Mountains. What's more, Pleasant Valley offers many different programs for people of all ages and abilities, including birding, canoeing, paddling and more.

    Visitors say there are so many hiking loops to choose from that it would simply be impossible to do them all in one day. Luckily, the staff in the nature center can help groups decide which trails would suit them best and where they might find beavers along the way.

  • #8
    Jiminy Peak Mountain Resort
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    #8 in The Berkshires
    Amusement Parks, Hiking, Recreation, Skiing
    TYPE
    Half Day to Full Day
    TIME TO SPEND
    Amusement Parks, Hiking, Recreation, Skiing
    TYPE
    Half Day to Full Day
    TIME TO SPEND

    This four-season resort in the town of Hancock is constantly bustling with visitors eager to try its many activities. The largest ski and snowboard resort in southern New England, Jiminy Peak offers a variety of winter sports, including snowshoeing, and lessons for all ages and levels. As the snow melts away, Jiminy Peak transitions into a summer mountain adventure park. Among the attractions are an alpine slide, a scenic chairlift ride, a rock climbing wall and the self-guided Aerial Adventure Park, which features six elevated courses. Plus, several hiking trails offer views of Mount Greylock and the Jericho Valley. Families with children enjoy spending time at this resort together. Recent travelers applauded the wide range of activities for children and adults and the reasonable prices.

    The resort is open year-round, but hours for each activity and facility can vary. Prices for the adventure park and ski lift also vary based on age, time and activities. For information on pricing, visit the Jiminy Peak website.

  • #9
    Herman Melville's Arrowhead Museum
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    #9 in The Berkshires
    Hiking, Museums, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Hiking, Museums, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    Restored by the Berkshire County Historical Society, the home of "Moby-Dick; or, The Whale" author Herman Melville is open to visitors interested in learning more about the literary legend. Located in the historic town of Pittsfield, the house was inhabited by Melville from 1850 to 1863. Along with the home, visitors can tour the barn and surrounding grounds, which feature a farm and nature trail.

    Even some of Melville's biggest fans said they were surprised at the amount of new information they learned during their tours. Recent visitors appreciated the interesting stories shared by the site's knowledgeable tour guides, as well as the gift shop, which sells a variety of books about and written by Melville.

  • #10
    Ramblewild Adventure Park
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    #10 in The Berkshires
    Amusement Parks, Hiking, Recreation
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Amusement Parks, Hiking, Recreation
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    The Berkshires offers plenty of hiking opportunities to get your bearings on the ground, but Ramblewild Adventure Park enables visitors to experience the Massachusetts mountains from an entirely different altitude. This treetop adventure course challenges outdoor adventurers and beginners alike as they climb and weave through the obstacles in the hemlock groves of Feronia Forest. Ropes, ladders, bridges, swings and zip lines are among the 130 elements across the eight different routes that await visitors 45 feet above the forest floor. Along with its aerial park, Ramblewild also offers hiking trails and snowshoeing.

    Previous travelers visiting Ramblewild as a family say the aerial course is among the best things to do in the Berkshires. Reviewers credit the encouraging staff and breathtaking views as prime reasons to plan a trip. Visitors also appreciate the range of courses for all skill levels. Reviewers say the 3 1/2-hour timeslot enables visitors to try out a handful of courses and take in the landscape from different parts of the forest, all while getting a great workout.

  • #11
    Massachusetts Museum of Contemporary Art
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    #11 in The Berkshires
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    The Massachusetts Museum of Contemporary Art (MASS MoCA) in the town of North Adams features impressive visual and performing arts from both well-known and emerging artists. The diverse artwork including everything from sculptures to virtual reality to painting to photography. What's more, the museum hosts more than 75 performances year-round, ranging from contemporary dance to outdoor silent films with live music. Whether you're looking to see art or make art, the MASS MoCA is sure to fuel your creative mind.

    Travelers say this industrial museum is a work of art in itself. This unique space offers so much eclectic artwork that reviewers report wandering its halls for hours. Visitors are especially impressed with the thought-provoking contemporary artwork and how each exhibit is strikingly different from the last, making for a memorable experience.

  • #12
    Norman Rockwell Museum
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    #12 in The Berkshires
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    The Norman Rockwell Museum walks visitors through the life and prolific works of the well-known American artist. Located in Stockbridge – the town Rockwell called home for the last 25 years of his life – the museum features a variety of exhibits displaying the artist's work, as well as his studio. In the museum cottage and surrounding grounds, festivals, workshops, speakers and galleries take place regularly.

    Reviewers recommend tagging along on a tour, in which knowledgeable guides give thoughtful insight into the painter and his artwork. Recent visitors also suggested strolling the attractive grounds and having a picnic instead of eating the meals offered on-site. Stockbridge is home to many fresh and locally-sourced restaurants; the famed Red Lion Inn is just down the street.

  • Naumkeag
    View all Photos
    Historic Homes/Mansions, Parks and Gardens
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Historic Homes/Mansions, Parks and Gardens
    TYPE
    1 to 2 hours
    TIME TO SPEND

    Read More »

  • Hancock Shaker Village
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    Historic Homes/Mansions
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Historic Homes/Mansions
    TYPE
    1 to 2 hours
    TIME TO SPEND

    Read More »

  • Berkshire Botanical Garden
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    Parks and Gardens
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Parks and Gardens
    TYPE
    1 to 2 hours
    TIME TO SPEND

    Read More »

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