From Boston Harbor in the east to The Berkshires in the west, Massachusetts is a state laden with compelling history and culture — and enticing ways for groups to explore the bounty of the past.
Whether groups are exploring Beacon Hill before an elegant meal, bounding through The Berkshires and its bevy of artistic offerings or investigating all points in between, the state is a veritable trove of portals to the past that prompt fun times and connection. Massachusetts is simply hard to beat when it comes to charm, history and a timeless elegance that discerning travelers are certain to appreciate.
Boston and Cambridge
Few cities in North America can match Boston’s bounty of old-world charm, making it an ideal escape for upscale groups on the lookout for elegant experiences and historical exploration.
Boston’s global name recognition carries immediate cachet with affluent travelers, said Emily Meehan, tourism sales manager for Meet Boston.
But what many groups might not be aware of is the city’s endless slate of group offerings that range from exclusive spectator sports to high-end cultural tours and elegant outings into Boston Harbor and beyond.
“This is a destination that understands luxury travel,” Meehan said.
Sports lovers will relish outings tied to the city’s storied athletic past, highlighted by options like VIP tours of TD Garden Sports Museum, home to the Celtics, and experiences at legendary Fenway Park, such as trying on authentic player uniforms and trying out an official MLB batting cage.
Getting on the water is always a memorable event, and groups can sail in sophisticated fashion with Classic Harbor Line, luxuriating aboard the 110-foot Northern Lights yacht or the 80-foot Adirondack sailing ship. Private cruises can even include catering, a bar and live music upon request, adding up to an enchanting and elegant soiree on the bay.
Across the Charles River, the city of Cambridge offers a “rich mix of culture, history and outdoor experiences,” said Candice Beaulieu, executive director for the Cambridge Office for Tourism. She added that groups also love the dining scene — boosted by eight restaurants highlighted in the Michelin Guide — as well as a lodging landscape showcasing “distinctive hotels that range from historic and boutique to full-service luxury.”
And for group outings that elevate an itinerary, she suggested a cruise with the Charles River Boat Company, taking in a live performance at Harvard’s acclaimed American Repertory Theater or a stroll through historic Mount Auburn Cemetery, America’s first garden cemetery.
Cape Cod
Bill DeSousa-Mauk, public relations manager for the Cape Cod Chamber of Commerce for nearly three decades, truly has his finger on the pulse of the region and on its appeal for groups seeking seaside scenery and serenity.
“The cape is a pretty laid-back place,” he said. “When you think about Cape Cod, you think of beautiful beaches, seaports, 15 towns with period homes and architecture, and a place that is so traditional people have been returning for generations.”
When it comes to unforgettable group experiences, DeSousa-Mauk points out there’s an endless array, but a few truly stand out for making memories.
“Whale-watching tours are quite popular and quite dramatic,” he said. “I’ve even seen people crying on them, they’re such majestic animals. It’s really quite an experience.”
Another group trek sure to make an impression is hopping aboard the Cape Cod Central Railroad and enjoying one of its special offerings.
“They have dinner trains, foliage trains and other themed outings where you can go through cranberry bogs and have dinner passing through various villages,” DeSousa-Mauk said.
He added that the cape’s various charming communities are a draw in themselves. “There are 15 towns, and each one is completely different and distinctive. Provincial towns that look back to when people lived differently than they do now.”
In fair weather, he highly recommends Art’s Dune Tours, including the popular sunset outing, where dinner and a bonfire can be added onto the experience.
“Provincetown has these huge sand dunes a hundred feet high,” he said. “It’s like being on the moon — a truly unique experience.”
Salem
Only a short drive north of Boston on the North Shore, Salem is known for the witch trials held there in 1692 and 1693, but today the city is all about bewitching visitors with a blend of culture, scenery and sophistication.
“Salem pairs American history with a surprisingly refined, modern sensibility,” said Ashley Judge, executive director for Destination Salem. “It’s walkable, coastal and visually striking, but it also has real substance.”
What distinguishes Salem for upscale groups is its collection of elevated, only-here experiences, Judge said. The Peabody Essex Museum stands out for its world-class curation and modern design, offering private tours that feel both intimate and intellectually engaging. On the water, Sunset Sail Salem delivers a tailored coastal perspective that is relaxed, elegant and perfect for groups seeking something memorable. Culinary travelers gravitate toward Salem Food Tours, which weave together local flavor and history in a way that feels immersive rather than scripted.
The city also excels at offering unexpected, artful moments, she said. Workshops at The Sea Wych Salem and personalized aura photography sessions at Ascend introduce visitors to Salem’s modern spiritual culture with a clean, contemporary aesthetic. Shopping is equally elevated, from Jenni Stuart Fine Jewelry’s custom pieces to HausWitch Home + Healing’s modern approach to spiritual retail.
Spring and summer amplify Salem’s appeal even further. Brick sidewalks lined with cafe tables, sailboats filling the harbor, and historic homes glowing in late daylight forge a quintessential New England atmosphere. Waterfront dining at Finz or Sea Level Oyster Bar, rooftop evenings at The Hotel Salem, and the bustling Salem Farmers Market all offer seasonal coastal charm that feels made for groups.
Springfield and Pioneer Valley
Springfield, the largest city in the Pioneer Valley region, shows off numerous ways to explore days of yore and counterbalances the area’s rural charms with its cosmopolitan flair.
“You have quaint New England towns and then a livelier big town like Springfield, with a casino and high-end steakhouse,” said Michele Goldberg, vice president of marketing for the Greater Springfield Convention & Visitors Bureau.
For a more active agenda, groups can visit Forest Park, a 735-acre outdoor oasis overlooking the Connecticut River, for breathtaking hiking, biking and other open-air fun. The park is home to aquatic gardens and ponds, wooded walking paths, sports and picnic areas, and even a zoo.
As for culture and history, groups need look no further than the Springfield Museums, which form a five‑museum campus in downtown covering art, history, science and the world of Dr. Seuss. One admission grants access to all five museums, plus an outdoor art offering sure to captivate guests.
“There’s a beautiful sculpture garden with all the [Dr. Seuss] characters, an art museum, history museum, and one of the largest cloisonné collections around,” Goldberg said. She added that groups can admire works by Monet, creations by Currier and Ives, and much more — and that the museum grouping is a Smithsonian affiliate. Groups of 10 or more can even customize their own docent-led tour focused on a particular theme, such as art, history, science or Dr. Seuss.
In nearby Deerfield, Goldberg strongly recommended a visit to Yankee Candle Village, which has a natural pull for groups thanks to its mix of immersive spaces, hands‑on activities and easy logistics. Guests can explore the Bavarian Christmas Village, enjoy make‑your‑own candle stations and wander through themed rooms that appeal to all ages.
She also touts Springfield’s central location near the middle of Massachusetts, resulting in a locale that feels removed without the necessity of major travel.
“We’re super easy to get to and very convenient to some major cities but without a lot of traffic,” Goldberg said.
The Berkshires
Further west, The Berkshires claim a blend of culture and countryside that few regions anywhere can approach. This unique regional “juxtaposition” is what really put the location on the map for discerning travelers, said Lindsey Schmid, senior vice president of tourism and marketing and regional tourism council director for 1Berkshire.
“We have all these high-end cultural offerings in rural settings,” she said. “Groups can go from hiking in the woods to a fancy meal.”
On the cultural end, Schmid points out renowned options such as MASS MoCA in North Adams, one of the largest contemporary art museums in the nation.
“It’s a very cool campus, and they love working with groups,” Schmid said. “There’s a brewery, a little cafe, and they’ll craft experiences for groups. You can even do after-hours events.”
Also in the northern part of the region is the Clark Art Institute, set on 140 acres and an easy win for groups because it blends world‑class art with a beautiful, walkable campus in Williamstown. Groups can enjoy guided tours tailored to their interests; explore galleries featuring European and American masters; and spend time outdoors on the expansive grounds that offer trails and reflecting pools.
A smaller but equally beloved offering is the Norman Rockwell Museum in Stockbridge. The museum honors the famed artist, known for his iconic Saturday Evening Post covers, with permanent and changing exhibits, and the museum will feature a special Calvin and Hobbes collection on display this summer.
For an escape to an earlier time in New England, the Hancock Shaker Village is a veritable living museum that includes a farm and much more, always alive with activity. Schmid mentioned the venue’s allure has been even more heightened lately due to its status as the filming location for “The Testament of Ann Lee” movie, starring Amanda Seyfried.
There are also historic homes in the region open for tours and exploration, including The Mount, the home of author Edith Wharton, and Naumkeag, a Gilded Age mansion nestled on 48 acres.
For summer trips, groups should plan ahead for the massively popular Tanglewood Music Festival, showcasing classical tunes (including from the Boston Symphony Orchestra) in July and August. And for pure pampering, consider a spa day at the famed Canyon Ranch wellness resort in Lenox.
