Summer in the Berkshires offers a unique cultural experience, marked by world-class music, art, and theatre performances. Whether you’re a first-timer or a seasoned visitor, we’ve curated the top activities to enrich your summer getaway. Prepare to immerse yourself in a vibrant and enchanting world!

Spectators at a theater performance facing the stage.

1. Captivating Performances

  • Shakespeare & Company is a professional live theater company nestled in the heart of the Berkshires, offering a vibrant summer season that showcases Shakespeare’s works alongside a diverse selection of classic and contemporary plays. Their productions are known for their high-quality performances, talented casts, and innovative interpretations, making each show a memorable experience for audiences. The company also hosts a variety of educational programs, workshops, and events that further enrich the cultural landscape of the Berkshires.
  • For seven decades, the Tony Award-recognized Williamstown Theatre Festival has brought together emerging and professional theater artists in the Berkshires for a thrilling summer festival. This festival features diverse world premieres, bold revivals, and a rich array of cultural events. Renowned artists such as Matthew Broderick, Audra McDonald, and Uma Thurman have graced the stage, while many others, including Chris Pine and Brie Larson, began their careers here.
  • The Berkshire Theatre Group is a prominent cultural institution in the Berkshires, dedicated to enriching the region’s artistic landscape through dynamic theater productions and educational programs. With a history spanning over nine decades, the group operates multiple venues, including the Fitzpatrick Main Stage and The Unicorn Theatre in Stockbridge, and the Colonial Theatre in Pittsfield. Known for its diverse repertoire, which ranges from classic plays to contemporary works and musicals, the Berkshire Theatre Group attracts top-tier talent and fosters the development of emerging artists. Their commitment to excellence and community engagement makes them a cornerstone of the Berkshires’ vibrant arts scene.
Closeup of musicians playing a guitar and the drums.

2. Harmonious Melodies

  • Berkshire Opera Festival (BOF) is a premier summer festival that has been enriching the Berkshires’ cultural scene since its inaugural season in 2016. As a fully-producing festival, BOF stages captivating operatic productions alongside recitals and a variety of related musical events. Committed to upholding the highest standards of artistic excellence, BOF has successfully revitalized the tradition of fully-staged opera, cementing its status as a key player in the Berkshire arts community. Through its dedication to quality and innovation, BOF continues to attract opera enthusiasts and contribute significantly to the region’s vibrant cultural tapestry.
  • Berkshires Jazz, Inc. is a non-profit organization dedicated to fostering a vibrant jazz scene in Berkshire County. They promote and preserve the rich tradition of jazz music through a variety of year-round performances and educational programs. Their events, which feature both local talents and renowned jazz artists, take place at various locations across the Berkshires, ensuring widespread community access and engagement. In addition to concerts and festivals, they offer educational initiatives designed to inspire and nurture the next generation of jazz musicians.
Women looking at art in a museum

3. Inspiring Exhibits

  • The Clark Art Institute features an array of special exhibitions every summer. These exhibitions offer a glimpse into a wide range of artistic expressions and historical perspectives, enriching the cultural landscape of the Berkshires. Beyond the exhibitions, visitors can immerse themselves in the institute’s permanent collection galleries, which house an impressive selection of paintings, sculptures, and decorative arts spanning centuries. The Clark’s expansive 140-acre campus invites exploration with scenic trails that meander through picturesque landscapes, offering opportunities for both relaxation and outdoor activities. Throughout the summer season, the institute hosts a vibrant schedule of events catering to diverse interests and ages, from lectures and workshops to family-friendly activities and musical performances, ensuring there’s something for everyone to enjoy.
  • Established in 1969 with the support of Norman and Molly Rockwell, the Norman Rockwell Museum celebrates American illustration art’s influence on society. Accredited by the American Association of Museums, it stands as the Berkshires’ foremost cultural attraction, dedicated to preserving and studying Norman Rockwell’s impactful contributions. The museum houses the world’s largest collection of Rockwell’s work, featuring 998 original paintings and drawings that reflect American life and values.
 Save Download Preview Dusk at Pontoosuc Lake in the Berkshires Hills of Western Massachusetts

4. Scenic Landscapes

  • Spanning 1,158 acres, Jug End State Reservation and Wildlife Management Area is renowned for offering some of the most breathtaking scenic vistas in the Berkshires. Its extensive network of trails provides outdoor enthusiasts with opportunities for hiking, birdwatching, and nature photography amidst pristine natural surroundings. Whether exploring the diverse wildlife habitats or simply enjoying the panoramic views from its peaks, Jug End offers an immersive outdoor experience that showcases the region’s natural splendor.
  • Encompassing over 1,000 acres of pristine woodlands, fields, streams, ponds, and a majestic waterfall, Greylock Glen stands as a haven for outdoor enthusiasts in the Berkshires. Its expansive landscape offers a wealth of recreational activities, including hiking along scenic trails that wind through diverse ecosystems and biking routes that traverse the glen’s picturesque terrain.
Drone shot of Hampton Terrace Inn, surrounded by green trees

5. Historic Lodging

Experience a slice of history and indulge in modern comforts at Hampton Terrace Inn, where the charm of the Gilded Age meets today’s luxuries. Enjoy the comfort of your room with amenities such as private baths, air conditioning, HDTVs, and free Wi-Fi. Begin your day with a delightful full breakfast buffet, included in your stay. Step back in time while enjoying every modern convenience—book your stay today for an unforgettable summer in the Berkshires.

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Stan Rosen

Stan Rosen has been the owner of Hampton Terrace for 26+ years. Originally from Georgia, Stan considers himself “still a tourist in his own home town” of Lenox. As a former member of the Berkshire Visitors Bureau Executive Committee for eight years, he is intimately familiar with most aspects of the Berkshires.