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Cool Things to do in the Berkshires for Families

A lovely spot in New England for a family getaway

The Berkshires is a beautiful and diverse region in Massachusetts, with plenty of things to do and see for families. Here are ten activities and attractions that you and your family can enjoy during a visit to the Berkshires.

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Mount Greylock

Mount Greylock is a must-see destination for families visiting the Berkshires region of Massachusetts. This beautiful mountain is the highest peak in Massachusetts and offers a wide range of activities and attractions for visitors of all ages.

Mount Greylock is a popular destination for hiking, camping, and picnicking. The mountain features several trails that offer breathtaking views of the surrounding landscape. The drive to the summit of Mount Greylock is a highlight of the region. The winding roads offer spectacular views of the Berkshire Hills and provide a great opportunity to take in the beauty of the area.

The summit can be reached via the Bascom Lodge and War Memorial Tower, both offer unique experiences. The War Memorial dedicated to the veterans of the Commonwealth of Massachusetts. Visitors can climb the tower for an unparalleled view of the surrounding landscape. The nearby Bascom Lodge is a historical landmark that offers a glimpse into the area’s past.

Mount Greylock is also a popular destination for winter sports, including cross-country skiing, snowshoeing, and sledding. The nearby Mount Greylock Ski Club offers alpine skiing and snowboarding. However, all year long the mountain is home to a diverse range of wildlife, including black bears, deer, and a variety of bird species. Families can enjoy a nature walk and explore the mountain’s rich ecosystem.

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Bash Bish Falls

Bash Bish Falls is a popular scenic spot located in the Taconic Mountains of Massachusetts, near the border with New York. It’s famous for being the highest single-drop waterfall in Massachusetts.

Bash Bish Falls is accessible by a moderate hike, the trail is about 1.5 miles round trip and takes about 1.5 hours to complete. It offers a beautiful view of the waterfall and the surrounding area. There are several picnic tables at the base of the falls and also designated areas for having a picnic. It’s a great spot to enjoy a meal with family and friends while taking in the view of the falls. It’s not recommended to swim at the falls because of the dangerous currents, however, swimming is allowed in the nearby Bash Bish Brook and Copake Lake.

There are campsites available nearby the falls, it is a great way to enjoy the outdoors and explore the waterfall at different times of day.

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Tanglewood Music Center

297 West Street, Lenox, MA 01240

Tanglewood Music Center is a music venue and educational institution located in the Berkshire Hills of western Massachusetts and is the summer home of the Boston Symphony Orchestra, and the Williamstown Theatre Festival.

Tanglewood is most famous for hosting the Boston Symphony Orchestra, which performs a series of concerts throughout the summer. It also features many other performances by renowned musicians and ensembles from around the world. They also offer free guided tours of the grounds and buildings, including the historic Tappan Mansion and the Leonard Bernstein Memorial. Additionally, the grounds are open for visitors during the day, a beautiful place for a walk or a picnic

Tanglewood hosts a variety of music education programs, including the Tanglewood Music Center, which is a training institute for young professional musicians, and the Tanglewood Festival Chorus, an auditioned group of singers from around the country. There is a museum that is open during the summer concert season which showcases the history of Tanglewood, the Boston Symphony Orchestra, and the Tanglewood Music Center.

Hungry? Tanglewood has several dining options available for visitors, from casual concessions to a more formal restaurant. Before you go, stop by the onsite shop that carries a variety of souvenirs and gifts, including music, books, and clothing

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Clark Art Institute

225 South St, Williamstown, MA 01267

The Clark Art Institute, located in Williamstown, Massachusetts, is a museum that specializes in European and American art, and also features outdoor sculpture, as well as special exhibitions, lectures, tours, and programs.

The Clark Art Institute website has a blog that provides updates on new exhibitions, events, and programs taking place at the museum, as well as essays and articles about art, artists, and the museum’s collection. The blog is called “Clark Chronicles” and can be accessed through the Clark Art Institute website.

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Massachusetts Museum of Contemporary Art

1040 Mass MoCA Way, North Adams, MA 01247

The Massachusetts Museum of Contemporary Art (MASS MoCA) is a contemporary art museum located in North Adams, Massachusetts in a restored19th century factory campus. The museum features works by established and emerging artists across a wide range of mediums, including painting, sculpture, film, video, and performance.

The MASS MoCA website has a blog called “The Inside scoop” which features updates on new exhibitions, events, and programs taking place at the museum, as well as essays and articles about art, artists, and the museum’s collection. You can also find information about upcoming shows and events, staff picks, and behind the scenes looks at the museum’s operations.

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Edith Wharton’s home

2 Plunkett St, Lenox, MA 01240

The Mount is a historic house and estate located in Lenox, Massachusetts. It was the home of Edith Wharton, an American novelist, short-story writer, and designer. The Mount is now open to the public as a house museum and cultural center.

Visitors to The Mount can take guided tours of the house and gardens, which provide a glimpse into the life and work of Edith Wharton. The tour includes the main house and the studio where she wrote many of her novels, as well as the beautiful formal gardens designed by Wharton herself.

The Mount also offers various programs and events throughout the year, such as lectures, workshops, and literary events, related to Edith Wharton and her works. It also hosts various exhibitions related to the life and work of Edith Wharton, and the American decorative arts of the Gilded Age.

Additionally, the Mount’s gardens are a great spot for a picnic or a walk, it is well-maintained and open to the public.

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Mission House

19 Main St, Stockbridge, MA 01263

Built in the 1700’s by missionary John Sergeant, the Mission House is a historic landmark and one of the oldest houses in Stockbridge, MA. Today, you and your family can come to visit and learn more about Mohican culture, John Sergeant and his family as well as local history.

At the Mohican Miles exhibit you will learn more about Indigenous history as well as explore the Mohican Medicines garden with labeled plants in English, Mohican and Munsee.

For families, there are always interesting activities going on at the Mission House, including easy guided kid-friendly hikes, cozy fire pit gatherings, art-making, cooking classes and adventures. Every season offers a selection of family-friendly activities, so it is always a great time to plan your visit.

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Stockbridge Bowl

A man-made lake located in Stockbridge, Massachusetts. It offers boating, fishing, and swimming, with a beach area and a playground.

There are several boating options available at the lake such as canoe, kayak, and paddle boats rentals and is stocked with fish, such as bass, perch, and sunfish, making it a great spot for fishing enthusiasts.

For families, Stockbridge Bowl has a designated swimming area with a sandy beach for visitors to enjoy. There are plenty of picnic tables, grills and shelters located around the lake, perfect for enjoying a meal with family and friends as well as a concession stand that offers food, drinks and ice cream . There is also a playground available for children to play on and enjoy.

For the active families there are several hiking trails that run around the lake that offer beautiful views of the lake and the surrounding area and playing fields available for sports like softball and soccer, and a basketball court.

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Lake Onota

Opposite State Forest, the lake is a beautiful spot for swimming, and there are also boat rentals available for those who want to explore the lake by canoe, kayak, or paddleboat. Families will love the public beach which is a great spot to relax and enjoy the sun and sand as well as the playground facilities, like Onota park where kids can play and have fun. There are also several picnic areas around the lake where families can enjoy a meal and take in the beautiful surroundings.

There are several hiking trails that wind through the surrounding woods and offer great opportunities to explore nature. Fishing is permitted on the lake, and there are a variety of fish species that can be caught, including bass, perch, and pickerel. If your kids are older enough to ride bikes or roller-skate , you can enjoy a great lake view while cycling/ rollerblading around the lake.

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That’s A Wrap!

The Berkshires is a beautiful area of Massachusetts that makes for the perfect family getaway anytime of year. In addition to gorgeous nature to explore and enjoy, there is a plenty of art, culture and history to be experienced. So what are you waiting for?

To help you explore more of Massachusetts, check out our other posts.

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I am a busy mama with 3 delicious babies and a serious itch for travel and writing (when I am not bartending, that is)! After graduating from Cal State San Marcos with a B.A. in Communications, I decided to start a family and pursue a career in freelance writing. I created HotMamaTravel as an outlet to do what I love while sharing useful travel tips and inspiration with others. Our mission is to show parents how to master travel with kids, while keeping your Saturday-night selves. We call it "Family travel...with a twist".

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