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Top Ten Things to Do in The Berkshires in Summer: Your Ultimate Guide

Welcoming summer in the Berkshires of Massachusetts is like stepping into a vibrant tapestry of cultural, natural, and recreational activities. Known for its scenic beauty and artistic soul, The Berkshires offers a treasure trove of experiences. In this guide, we spotlight the top ten things to do in the Berkshires during the summer, ensuring you savor every moment of this enchanting season.

When you make it to Great Barrington, be sure to stop by and say hi at Fluff, the Berkshires Alpaca Store located at 319 Main Street, Great Barrington, MA! 

Top Ten Things to Do in The Berkshires in Summer: Your Ultimate Guide

1) Tanglewood Music Festival in Lenox

Summer in The Berkshires isn’t complete without attending a concert at Tanglewood. This iconic venue, famous for its lush lawns and extraordinary lineup, features performances by the Boston Symphony Orchestra and other renowned artists throughout the summer. There's nothing like sitting on the lush green lawn and soaking in the sounds of nature and beautiful music. Take a picnic blanket from our collection for the best time.

2) Appalachian Trail Adventures

Lace up your hiking boots for an unforgettable journey along The Berkshires’ stretch of the Appalachian Trail. This national scenic trail offers a mix of challenging hikes and gentle walks, all with stunning views. Gear up with our alpaca hiking socks to ensure a comfy, cool hike.

Top Ten Things to Do in The Berkshires in Summer: Your Ultimate Guide. A gilded age alpaca looks out the window of a fancy room.

3) The Mount – Edith Wharton’s Estate

 Explore the exquisite home and gardens of author Edith Wharton in Lenox. The estate not only celebrates Wharton's literary legacy but also hosts engaging cultural events throughout the summer. A must see for any fans of the Gilded Age. 

4) Art Exploration at MASS MoCA

North Adams’ MASS MoCA, a haven for contemporary art lovers, is a must-visit. Its dynamic exhibits and performances make it a pinnacle of The Berkshires' art scene.

Top Ten Things to Do in The Berkshires in Summer: Your Ultimate Guide. An Alpaca popping out of an inner tube in a lake surrounded by green landscape.

5) Aquatic Fun by the Berkshire Lakes: The Berkshires' lakes provide a peaceful retreat for swimming, boating, or just unwinding by the water. Spots like the Lenox Town Beach at Laurel Lake and Lake Mansfield in Great Barrington are popular choices for a serene day out on the beach with the whole family. 

Top Ten Things to Do in The Berkshires in Summer: Your Ultimate Guide. An alpaca dressed like a shakespeare character stands in a round theater

6) Watch Worldclass Theater

The Berkshires has loads of talented theaters. Shakespeare and Company in Lenox is known for their Shakespeare, but also puts on a selection of other genres during their summer season, including great shows for families. Check out Williamstown Theatre Festival in Williamstown, where new productions are often birthed. It's a hotbed for theatrical innovation and star-studded performances.

7) Historic Home Tours and Lush Gardens

Discover the history and beauty of The Berkshires through its historic homes and gardens. Estates like Naumkeag and Chesterwood offer a glimpse into the past amid stunning natural beauty.

8) Cycling the Ashuwillticook Rail Trail

This picturesque trail, winding through the Berkshire landscape, is perfect for a leisurely bike ride, offering spectacular views and a refreshing summer breeze. Bike rental shops can be found around the trail for those who don't bring their own! 

Top Ten Things to Do in The Berkshires in Summer: Your Ultimate Guide. An alpaca standing in the middle of a farmer's maket.

9) Great Barrington Farmers' Market Delights

Immerse yourself in local flavors at farmers' markets throughout The Berkshires. The Great Barrington market is renowned for its fresh produce and artisanal treats. 2024 hours are every Saturday, from 9AM to 1PM, May 11th – November 9th. 


Top Ten Things to Do in The Berkshires in Summer: Your Ultimate Guide. An alpaca stands on a platform at an aerial adventure park.

10) Aerial Adventure Parks: For thrill-seekers, Jiminy Peak in Hancock provides exhilarating summer activities like mountain biking and an aerial adventure park. A short trip across the state line into New York, the Catamount Ski Resort transforms in the summer into an Aerial Adventure Park. A great activity for families looking to burn some energy! 

From the lush, green hills to the rich cultural tapestry, The Berkshires in summer is a destination that offers something for everyone. These top ten activities highlight the best of what The Berkshires has to offer, ensuring your summer is filled with unforgettable experiences. Plan your trip today and discover the unique charm of The Berkshires in the summertime!

Need more tips for where to stop around Great Barrington and The Berkshires? Find them here!

Travel Tips: Always check for the latest opening hours and health guidelines to ensure a safe and enjoyable visit to The Berkshires’ top summer attractions. Enjoy your journey through the heart of New England’s summer paradise!