Although it’s one of the smallest states in the country, Massachusetts is big on fun for visitors. The state is filled with activities, culture, scenery, history and much more.
From art colonies to historic landmarks and beaches, group travel planners will find activities to engage all their customers in one of the nation’s oldest states. Come along to explore the small but mighty state of Massachusetts and uncover some of its hidden gems.
The Berkshires
In the west of Massachusetts is Berkshire County, often referred to as the Berkshires. This county is made up of 30 towns and two cities. Though it is most widely known for outdoor adventures, the Berkshires has a very strong cultural scene as well.
“What sets the Berkshires apart from other travel destinations is the combination of access to outdoor recreation and to see world class shows, go play and dance, and see the largest contemporary museum in the country,” said Lindsey Schmid, senior vice president of tourism and marketing for 1Berkshire. “There’s a variety of activities for any traveler.”
The Massachusetts Museum of Contemporary Arts is located in Adams, Massachusetts. Visitors can view myriad rotating exhibits along with permanent pieces by artists from around the world.
ArtWeek Berkshires, a 10-day festival celebrating all forms of art all across Berkshire County, made its post-pandemic return in September 2022. The fete comprised over 100 events, including open studios, live performances, poetry readings, painting demos and gallery openings.
For travelers who love outdoor activities like hiking, this region is definitely the ideal destination. Bash Bish Falls in Mount Washington has one of the area’s easiest trails with a breathtaking 59-foot split waterfall at the end. However, this is a very popular, high traffic site. Trekkers could also opt for the less known Hoosac Range near North Adams, which has trails with gorgeous sunset views and hikes that range from easy to hard.
“More main hiking trails were overused during the pandemic,” Schmid said. “So we suggest to travelers that some of our smaller, less known trails could be visited more.”
Boston
Formerly dubbed the “Athens of America,” Boston is an East Coast metropolis with innumerable activities, events and eateries.
The city is a sports powerhouse. Its five professional teams — the Celtics (basketball), Bruins (hockey), Red Sox (baseball), Patriots (football) and Revolution (soccer) — have all won national championships within the past decade.
Aside from athletics, Boston is also lauded in the culinary world for some of its staple dishes. Travelers can head to Mr. Dooley’s for authentic Boston baked beans. They can also weigh in on the citywide debate about who makes the best cannoli by trying the treats at both Modern Pastry and Mike’s Pastry. For something more upscale, Menton, located in the Four Point neighborhood, may be more fitting. Many people speculate that this modern fine dining eatery would be a Michelin star restaurant if there were a Michelin guide for Boston.
Naturally, no group should visit Boston without visiting Griffin’s Wharf, the site of the historic Boston Tea Party in 1773. This event is cited as the first major act of rebellion by colonists toward Great Britain, which eventually led to the formation of the United States.
Plymouth
One cannot mention Plymouth without also mentioning Plymouth Rock, one of the most iconic historical landmarks in the United States. It is known worldwide as the landing point for the pilgrims in 1620, though seeing it in person may be a bit underwhelming.
“The significance of Plymouth Rock is more impactful than the actual site,” said Brian Logan, director of communications for See Plymouth. “While the National Monument to the Forefathers is as grand as it is important. At 81-feet tall, it’s the largest granite monument in the United States.”
Designed by Boston sculptor Hammatt Billings, the National Monument to the Forefathers shows human figures representing the virtues of faith, morality, education, law and liberty.
Like most regions in Massachusetts, Plymouth County includes many communities: 26 towns and the city of Plymouth. Starting at the Plymouth Visitor Center, groups can take a self-guided tour using Action Tour Guide, a virtual guide using audio, maps and a book, to lead themselves through the city while stopping at sites like a Mayflower replica, Plymouth Rock and a statue of Chief Massasoit, where they will learn about the true relationship between the pilgrims and the Wampanoag tribe.
“We also have a great free mobile app called See Plymouth,” Logan said. “It’s available for your Apple or Android phone, and it can be used to make planning your trip even easier.”
Gloucester
Gloucester is a city known for its natural beauty, breathtaking beaches and fresh seafood like lobster, scallops and especially tuna, thanks to the show “Wicked Tuna,” which is filmed there.
Travelers can take in the sparkling views of Smith Cove while dining at the Studio, a seafood restaurant in the Rocky Neck neighborhood. In addition to dining by the sea, visitors can also explore the open waters on schooners, cruise ships, charter boats or even go whale watching. Experts say the best time to visit for whale watching is between May and October.
This year also marks a major milestone for Gloucester, as the city brings in its 400th anniversary. Special events will be scheduled throughout the year in anticipation and observation.
“We’re celebrating it as 400-plus years to also acknowledge the Indigenous people who were here before the settlement,” said Tess McColgan, executive director of Discover Gloucester.
Aside from maritime attractions, Gloucester also has many things to do on land, including visiting Halibut Point State Park; spending time in Rocky Neck, an active art colony with artists using their homes as galleries; or going downtown and shopping on Main Street, where Generous Gardeners, a nonprofit organization, maintains the plants year-round.
“Discover Gloucester also has a “Plan Your Visit” tool, which is an itinerary planner for before you come or while you’re already here,” McColgan said. “The itinerary you create can be shared with your entire group. It also gives trip inspiration, or you can create your own from scratch.”
Cape Cod
Cape Cod is located at the southernmost point of New England. It has 15 towns, as well as the islands of Nantucket and Martha’s Vineyard, and can only be reached by the Sagamore Bridge or Bourne Bridge. The cape is home to 52 harbors and occupies 559 miles of coastline. It is also home to over 130 beaches ranging from family friendly to a surfer’s paradise.
“The views crossing into the cape are breathtaking, and the water has healing powers,” said Patti Lloyd, senior vice president of sales at the Cape Cod Chamber of Commerce. “We’re very conscious of how the water is treated and used to keep it pure.”
Cape Cod is great for escaping the daily woes and just enjoying nature. The attractions are also entertaining for all ages, from toddlers to seniors.
Heritage Museums and Gardens in Sandwich features 42 classic American automobiles, the oldest being an 1899 Winton Motor Carriage. In the gardens, visitors can find several “bee hotels” for solitary bees. The hotels are to keep the bees fed so they can in turn help pollinate the gardens and organically keep unwanted insects away.
For even more flower power, groups can plan their Cape Cod visits to coincide with the Hydrangea Festival July 7–16, where the area’s signature pink, blue and white hydrangeas will be on full display. Private tours of homeowners’ gardens, lectures and workshops can also be expected.
The National Seashore offers more than 43,000 acres of beaches, woods, ponds, and hiking and biking trails, with close to 40 miles of Atlantic shoreline. Groups will also be delighted to see lighthouses, cultural landscapes and wild cranberry bogs along the way.
“Don’t just take a day trip,” Lloyd said enthusiastically. “Spend many days. We like to say Cape Cod is a short trip to far away. There are so many things to do. You can’t fit it all into one day.”
