Culture, history, hospitality and outdoor adventure come together across Western Massachusetts

The Berkshires offers groups an exceptionally versatile New England destination with turn-key logistics and broad market appeal. Across four distinct seasons, the region seamlessly pairs full-service group accommodations and motorcoach-friendly infrastructure with diverse, turn-key attractions—spanning world-class contemporary art and Gilded Age estates to living history museums and mountain adventures. Whether crafting multi-day itineraries for student groups, adult leisure tours, or corporate retreats, operators can easily build balanced programs that deliver unforgettable experiences and reliable, year-round client satisfaction.

Stretching from North Adams in the north to Great Barrington and the communities of the southern Berkshires, a group itinerary can combine contemporary art one day with American history, Gilded Age architecture or an outdoor adventure the next.  1Berkshire has highlighted 10 places that illustrate the range of experiences available to groups traveling through the region.

Start with Lodging

1. Fairfield Inn & Suites

Great Barrington serves as an ideal basecamp for exploring the southern Berkshires, surrounded by vibrant downtown dining and shops. Beyond its prime location, the property excels at facilitating seamless group stays with tailored check-in, ample motorcoach parking, and inclusive morning dining, letting visitors spend less time coordinating and more time immersing themselves in the surrounding region.

2. Hotel Downstreet

Set in downtown North Adams, Hotel Downstreet immerses groups directly in the city’s creative movement. The property uses contemporary art installations, local historic design elements, and community-driven spaces to create an inspiring atmosphere that connects travel groups directly to the region’s lively cultural scene right from their lobby.

Hotel Downstreet (Photo credit: Corey Favino)

3. The Porches Inn at MASS MoCA

Located directly across from MASS MoCA, The Porches Inn offers a distinctive historic lodging experience built from renovated 19th-century Victorian row houses. The inn pairs architectural heritage with modern boutique comforts, providing groups a cozy, character-rich retreat featuring inviting fireplaces and relaxing outdoor gathering spaces after a full day of arts exploration.

Porches Inn (Photo credit: Corey & Erin McGinn)

4. The Red Lion Inn

A quintessential landmark in historic Stockbridge, The Red Lion Inn delivers timeless New England hospitality that famously inspired artwork by Norman Rockwell. Beyond its classic porch and antique-filled halls, the property offers authentic group dining and customized stay packages that anchor any itinerary in traditional Berkshire heritage.

Red Lion Inn (Photo credit: Barry Winiker)

Now, Complete Your Itinerary

5. Catamount Mountain Resort

Straddling the Massachusetts-New York border, Catamount Mountain Resort provides thrilling year-round outdoor adventures tailored for energetic group outings. From leaf-peeping scenic chairlift rides and treetop aerial adventure courses in the warmer months to alpine skiing and tubing in winter, it offers shared excitement against dramatic mountain backdrops.

Ziplining on Catamount (Photo credit: 1Berkshire)

6. Hancock Shaker Village

Hancock Shaker Village offers an immersive journey into historic American design, farming, and communal living across 20 preserved structures, including the famous Round Stone Barn. Guided group tours bring the village to life through interactive craft demonstrations, heritage livestock encounters, and stories of Shaker innovation and craftsmanship.

Hancock Shaker Village (Photo credit: Kate Elaine Photography, courtesy of 1Berkshire)

7. MASS MoCA

As the largest contemporary arts museum in the nation, MASS MoCA transforms a sprawling 19th-century factory campus into an extraordinary artistic playground. Its vast, light-filled galleries host immersive, large-scale installations and world-class exhibitions that spark inspiration and group conversation around every corner.

MASS MoCA (Photo credit: Courtesy of 1Berkshire)

8. Naumkeag House & Gardens

Naumkeag highlights the grandeur of the Berkshires’ Gilded Age era through its vibrant architectural style and world-famous landscape gardens. Groups can enjoy special seasonal events or tour stunningly preserved interior rooms before strolling through terraced gardens that capture the serene elegance of countryside estate living.

The Naumkeag Tulip Show (Photo credit: Barry Winiker)

9. Norman Rockwell Museum

Home to the world’s most extensive collection of original Norman Rockwell artwork, this Stockbridge museum celebrates American illustration and visual culture. Guided group tours provide intimate glimpses into Rockwell’s artistic process inside his preserved studio, showcasing timeless stories and iconic imagery that resonate across generations.

10. Tanglewood

Renowned as the summer home of the Boston Symphony Orchestra, Tanglewood delivers world-class musical experiences amidst beautifully manicured grounds. Groups can enjoy concerts on the lawn or in the shed throughout the summer and educational talks and concerts at the Tanglewood Learning Institute the rest of the year.

BUILDING A BERKSHIRE GROUP ITINERARY

The variety of these 10 destinations also illustrates one of the practical advantages of group travel in the Berkshires: an itinerary does not have to revolve around a single interest.

Every season brings its own distinct highlights to these destinations. Hotel stays serve as ideal launchpads for year-round excursions, historic properties frame changing scenery, museum visits offer climate-controlled cultural immersion, and mountain destinations provide elevated views and seasonal activities throughout the year.

For tour operators and group planners, this rich diversity makes crafting exceptional itineraries effortless. Whether curating a journey centered around fine arts, rich history, farm-to-table dining, thrilling outdoor recreation, or an inspiring fusion of all four, the distinct charm of each Berkshire community transforms a simple trip into an unforgettable voyage of discovery.

About The Berkshires:

Less than three hours from New York City and Boston, the Berkshires offer culture and adventure year-round. The surrounding mountains provide plenty of opportunity for outdoor excursions in all seasons while world class culture and entertainment, along with a deeply rooted food culture and an array of lodging options amidst picturesque towns, set this region apart. The Berkshires is a picturesque rural destination with a cultural scene to rival far larger urban dwellings.

About 1Berkshire:

1Berkshire is a county-wide marketing and economic development organization that works to simultaneously preserve, position, and promote Berkshire County’s profound sense of place. Its mission is to advance Berkshire County’s economy by advocating for the business community and attracting visitors. Powered by membership, 1Berkshire provides programs that connect businesses with resources and potential customers, as well as develop future leaders and support entrepreneurs.

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Last modified: October 23, 2026