Top 10 Spots for Groups in the Berkshires

Get On Board!

The Berkshires offers a blend of culture, history, and natural beauty that few other regions can match. From world-class museums to iconic New England lodging, the Berkshires provides a seamless destination for groups of all sizes. Whether your itinerary focuses on the vibrant arts scene in the northern Berkshires or the historic elegance of the southern Berkshires, the region’s hospitality and variety of attractions make trip planning easy and rewarding.

Here are ten exceptional venues that belong on every Berkshire group tour itinerary:

No good itinerary is complete without perfect lodging 

1. Fairfield Inn & Suites

The Fairfield Inn & Suites located in Great Barrington, offers a comfortable and convenient home base for groups exploring the region. With modern amenities like complimentary breakfast and an indoor pool, it provides a relaxing retreat with easy access to the town’s vibrant downtown shops and dining. Did you know? Great Barrington was named one of the best small towns in America, making it the perfect starting point for groups looking to experience the charm of the Berkshires.

2. Hotel Downstreet

Located in the heart of North Adams, this hotel offers a modern, upscale lodging experience that is perfect for groups visiting the Berkshires. Its walkable location provides convenient access to local dining and shops, making it an excellent base for groups that want to stay in the middle of the action while enjoying comfort and contemporary amenities. Did you know? This property reimagines the classic American motor lodge, blending retro style with contemporary comfort.

Hotel Downstreet. Photo by Corey Favino.

3. Hotel on North

Hotel on North is a sophisticated downtown Pittsfield boutique property which is perfect for groups. With its restored historic architecture and modern amenities, it’s a stylish home base within walking distance of theaters, galleries and dining and its central location makes it easy to get to anywhere in the Berkshires. Did you know? The hotel seamlessly merges two 19th-century buildings, preserving their unique character while offering contemporary luxury.

4. The Porches Inn at MASS MoCA

This unique collection of renovated Victorian houses offers an upscale, boutique experience that groups will love. Located just steps from MASS MoCA, the inn blends historic charm with modern luxury. It is an ideal spot for groups seeking a character-filled stay that reflects the artistic and historic spirit of the Berkshires. Did you know? The inn is created from a collection of renovated 19th-century Victorian houses, offering a unique, charming village feel.

5. The Red Lion Inn

A historic landmark in Stockbridge, the Red Lion Inn is the quintessential New England experience. With its rich history and legendary hospitality, it is an ideal location for groups looking to enjoy classic American dining in a warm, inviting atmosphere. Its central location makes it a perfect hub for touring the southern Berkshires. Fun fact: This landmark is so iconic that Norman Rockwell immortalized it in one of his famous paintings

Complete your itinerary with memorable experiences

6. Hancock Shaker Village

For an interactive and educational experience, nothing beats Hancock Shaker Village. Groups can explore over 20 historic buildings, learn about Shaker life, and enjoy the beautiful grounds and heritage breed animals. It is a fantastic destination for groups interested in hands-on learning, history, and farm-to-table cultural connections. Fun fact: The village is famous for its seasonal “baby animals” program, a must-see for groups visiting in the spring.

7. MASS MoCA

As one of the largest centers for contemporary visual and performing arts in the United States, MASS MoCA is a must-see for any group. The museum’s expansive, airy galleries can accommodate large groups comfortably, allowing travelers to explore bold, large-scale exhibitions at their own pace. It is a cornerstone of the Northern Berkshire cultural experience. Did you know? The museum is set within a massive, historic industrial factory complex, providing vast galleries that allow for unique, large-scale art installations.

8. Naumkeag House & Gardens

This Gilded Age mansion is a masterpiece of history and landscape design. Groups can tour the historic house with its original furnishings and then take a leisurely stroll through the renowned gardens. The site provides a captivating look at an era of grandeur and offers a perfect, scenic setting for group photography. Fun fact: The site features over 10 acres of gardens designed by Fletcher Steele, restored to capture their original Gilded Age splendor.

9. Norman Rockwell Museum

Home to the world’s largest collection of original Norman Rockwell paintings, this museum is a touchstone of American culture. The museum features changing American illustration exhibitions and offers a serene setting for groups. Its accessible gallery spaces and picturesque grounds provide a wonderful, reflective stop for any tour through Stockbridge. Did you know? The museum grounds are home to the artist’s original Stockbridge studio, which was moved to the site for visitors to explore.

10. Tanglewood

As the summer home of the Boston Symphony Orchestra, Tanglewood offers world-class musical performances in a breathtaking outdoor setting. Groups can choose to sit in the historic Shed or enjoy a picnic on the sprawling lawn. It is a premier cultural destination that promises an unforgettable, high-energy experience for music lovers of all ages. Fun fact: Beyond the performances in the summer, Tanglewood now offers year-round programming at the Tanglewood Learning Institute.

Start Planning Your Berkshire Itinerary Today 

The Berkshires is waiting to welcome your group for an unforgettable journey. To learn more about these locations and to begin mapping out your logistics, visit Berkshires.org. You can explore our events calendar, view group-friendly dining options, and use our planning tools to create a seamless itinerary that showcases the very best of our region.