12 Small Towns in Massachusetts With Big Charm
Massachusetts is a state of firsts. The first public park (1634), the first railroad (1826), and the first subway (1897) in the US were constructed in the Bay State. The first telephone call was between inventor Alexander Graham Bell and his assistant, Thomas Watson, in Boston in 1876. Most importantly, the first shots of the American Revolutionary War were fired in the small towns of Concord and Lexington.
From villages with historic significance like Salem and Provincetown to areas of natural beauty like Northampton and Stockbridge, these Massachusetts towns are as full of charm as the first US institution of higher learning, Harvard. So consider grabbing a bite of Dunkin Donuts, where the worldwide company first opened shop, and traverse the hills and beaches of glorious Massachusetts.
Northampton
Bounded by the Connecticut River and two gentle mountains, Mount Holyoke and Mount Tom Ranges, Northampton is widely regarded as "Paradise City." Only about 25 minutes from Springfield, Northampton was originally called "Nonotuck" from the Algonquian word meaning "middle of the river." The town was also in the middle of many historic events, such as brutal raids during King Philip's War (1675 to 1676) and Queen Anne's War (1702 to 1713), which the many museums of the town memorialize.
Northampton has attracted many free-thinking activists like abolitionists Sojourner Truth, William Lloyd Garrison, David Ruggles, and Frederick Douglass. Visitors can learn all about them in the David Ruggles Center. You can also learn about the 30th US president and former mayor of Northampton, Calvin Coolidge, in the Calvin Coolidge Presidential Library and Museum. Remember to find suitable lodgings at the Hotel Northampton.
Westford
Located about 20 minutes from Concord, the small town of Westford embodies simplicity and serenity. Rolling hills, lakes, and apple orchards characterize Westford's big charm for a small town of around 25,000 residents. Travelers can sample unique commodities, such as Westford's excellent apple products at the Apple Blossom Festival in May. Or, in the Strawberry Festival in June, treat yourself to strawberry shortcakes.
For action and adventure, try out the Nashoba Valley Ski area. Because Westford is best known as a bedroom community, settle down in the Westford Regency Inn and Conference Center.
Concord
Approximately 20 miles from Boston, the town of Concord embodies that New England spirit for any traveler to enjoy. Various Nipmuc groups of the native Massachusetts tribe called the land between the Assabet and Sudbury rivers "Nashawtuc" or "between the rivers." It was between those two rivers that the first battle of the American Revolutionary War commenced in 1775. Famed architect Daniel Chester French, who sculpted Abraham Lincoln's likeness at the Lincoln Memorial in Washington DC, designed the minuteman statue at Concord's Old North Bridge.
On the outskirts of town, in Sleepy Hollow Cemetery, renowned Transcendentalists and authors Louisa May Alcott, Nathaniel Hawthorne, Henry David Thoreau, and Ralph Waldo Emerson are buried in the town they came from. As a town teeming with historical relevance that shaped America, there are also a few great places to settle down: Concord's Colonial Inn, North Bridge Inn, and Residence Inn.
Salem
Not all the fine towns in Massachusetts were sites of goodness and joy. Midway between Boston and Rockport, the infamous witch trials of Salem from 1692 to 1693 have made the town a placename for tragedy and misfortune. Today, the Charter Street Cemetery/Old Burying Point commemorates the women hanged for condemnation. The Salem Witch Museum not only contextualizes and informs visitors of those infamous witch trials in Salem but also examines witch trials worldwide and why they occurred.
In addition, the Salem Heritage Trail is riddled with local landmarks that solemnize that period. Among these attractions are the Witch House, the Bewitched Statue, and the Salem Witch Village. If you prefer attractions unrelated to witches, consider touring the Hammond Castle Museum, the Pioneer Village, or a replica of an ancient seafaring vessel, The Friendship. Lastly, spend the night at The Cove at Salem, Hawthorne Hotel, and The Hotel Salem.
Rockport
Approximately 30 minutes from Salem, the seaside town of Rockport is a calming port town where you can view the silver expanse of Cape Ann. Travelers flock to Rockport for the sun and fun that the beaches offer. From Front Beach to Back Beach and Garden Beach to Pebble Beach, seagoers will revel in the many shores and waters surrounding Rockport. You might also be invested in touring three historic lighthouses that have shepherded ships to safe harbors. First, the Thacher Island Twin Lighthouses are the only fully operational multiple lights on the US East Coast. Second, the Straitsmouth Island Lighthouse.
Rockport is also known for being one of the oldest art colonies in America, where over thirty galleries can be perused in the Rockport Art Association and Museum. As a seaside town, Rockport boasts plenty of accommodations like the Lighthouse Lane Cottages, Rockport Inn & Suites, and The Emerson Inn by the Sea.
Lexington
Like Concord, about 6.5 miles away, the town of Lexington is known for being the first site to experience the American Revolution. There, the Battle of Lexington, or Battle Green, was fought, where "the first blood was spilled in the dispute with Great Britain," as George Washington wrote in his 1775 diary. On the original site of the Battle Green, the Revolutionary Monument and Minuteman Statue honor the brave American militia who clashed with the British.
Nearby, the Hancock-Clarke House documents the town's role in the American Revolution and conducts historic reenactments. You can pay homage to these fallen soldiers from both sides of the Revolutionary War at the Ye Olde Burial Ground. Or you can tour crucial military structures like the Belfry Terrace, Buckman Tavern, and Munroe Tavern. Before touring this historic town, pick a good place to rest, like The Inn at Hastings Park, Aloft Lexington, or Element Lexington.
Provincetown
Provincetown sits comfortably at the northernmost tip of Cape Cod, in a region once ruled by the Wampanoag and Nauset tribes. It was in 1620 that the Pilgrims from England aboard The Mayflower first landed and established their community alongside Plymouth. The Pilgrim Monument and the Provincetown Museum memorialize that momentous occasion.
Nowadays, Provincetown is widely known as a proud safe haven for members of the LGBTQ+ community. As such, Provincetown is best expressed through bohemian art exhibits and modernist displays at the Provincetown Art Association and Museum. As a seaside town, there is a need to gallivant through the Provincetown Dunes in the National Seashore Park. Most of all, do not forget to replenish and recharge in splendid establishments like Admiral's Landing, Ainsworth Cottages, and Anchor Inn Beach House.
Sandwich
With an official motto like Post tot Naufracia Portus, meaning "after so many shipwrecks, a haven," it is no small wonder that the town of Sandwich feels like a breath of fresh air. Since 1639, Sandwich has been one of the oldest towns on Cape Cod and in the United States. The Sandwich Glass Museum showcases exhibits and demonstrations of the town's glassblowing heritage. Likewise, Green Briar Nature Center and Jam Kitchen are sites of natural wonders and adventure for any outdoors person.
Sandwich is a snack worth savoring with a New England charm and dazzling aquatic attractions like the Scusset Beach State Reservation or Springhill Beach. So consider spending a few days in Sandwich at The Dan’l Webster Inn & Spa or Sandwich Lodge & Resort.
Stockbridge
Along the Housatonic River in the Berkshire Hills and about 15 miles from Pittsfield, Stockbridge is home to two of America's leading pioneers in art and culture. First is artist-illustrator Norman Rockwell, whose 25 years of his life in Stockbridge—alongside his numerous artworks—can be explored in the Norman Rockwell Museum. Second is the legendary sculptor Daniel Chester French. His sculpting studio and barn gallery can be best appreciated in Chesterwood.
Other historic edifices in Stockbridge include the Historic New England's Merwin House, Naumkeag, Ventfort Hall Mansion and Gilded Age Museum. Do not miss out on the best lodging in the area, The Red Lion Inn.
Oak Bluffs
On the island of Martha's Vineyard is the quaint town of Oak Bluffs. As a residential and resort community, Oak Bluffs sports many prominent beaches like Inkwell Beach. Additionally, the East Chop Lighthouse continues to guide numerous ferries traveling between the islands of Massachusetts and the mainland.
The Oak Bluffs Marina is the largest marina in Martha's Vineyard, where visitors can enjoy a few boating and fishing activities out in the vast open waters that trickle into the Atlantic Ocean. The town promotes the oldest continuously operating Flying Horse Carousel in the US. So spend some time away from the mainland by booking rooms at The Walker House.
Nantucket
A close neighbor to the Island of Martha's Vineyard is Nantucket Island. The main town there is Nantucket. The town and island derive the shared name from the Wampanoag word meaning "The Faraway Land." Certainly, much like Martha's Vineyard, it is about 30 miles from the south coast of Cape Cod. For many years, Nantucket was a major whaling port in North America. The Whaling Museum educates tourists of that particular period of whale-hunting.
Nowadays, people are more attracted to Nantucket's beaches like Jetties, Coatue, and Dionis beaches. You might also be attracted to the Brant Point Lighthouse. As a seaside town, Nantucket promotes many accommodations for visitors to stay a while, so pick a few options like Faraway Nantucket, White Elephant Nantucket, and Brass Lantern Inn.
Lenox
Only about 11 minutes from Stockbridge, Lenox is another serene town in the Berkshires. Even though the town of Lenox has no relation to the American manufacturing company Lenox, the town still produces many delights for travelers to enjoy. Visit Tanglewood, the summer home and retreat of the nationally renowned Boston Symphony Orchestra.
Tour The Mount, the garden home of Pulitzer Prize-winning novelist Edith Wharton. Trek through the magnificent Pleasant Valley Wildlife Sanctuary. Then, venture into Ventfort Hall, the most expensive private dwelling constructed during the Gilded Age of the 1890s. Because Lenox is most famous for the town's award-winning lodgings, get some pristine relaxation at Apple Tree Inn, Brook Farm Inn, or The Whitlock.
When legendary explorer John Smith came to Massachusetts, he named the land after the Massachusetts tribe that was widespread in the area. The name meant "near the great hill," and for many centuries after, the small towns of Massachusetts have prospered either around some of these great hills or out into the islands of the eastern coast. Wandering around these small towns is an enchanting experience. With Salem's dark past, Provincetown's status as an LGTBQ+ haven, Concord's and Lexington's heritage as the sites of a monumental war, and other fine settlements, the small towns of Massachusetts have as much big charm as the big cities of Boston and Quincy. So, like what Alexander Graham Bell said to his assistant, Thomas Watson, through the telephone, "Come here, I want to see you."
