Massachusetts's 11 Most Underrated Towns to Visit in 2024
As a state of firsts—the first telephone call, the first railroad, and the first shots of the American Revolutionary War—Massachusetts contains many popular and populated locations that you believe you should visit first. Most of the time, you skip the small towns and head straight to the sophisticated joys of Harvard and Boston. But Massachusetts’s most underrated towns are worth visiting this time of year.
From hidden villages in the sylvan hills of the Berkshires to haute seaside towns overlooking the Atlantic Ocean, these underrated small towns should at least be visited, if not the first place to go. So try not to be the last person who has not bothered sampling the cultural and natural amenities each underrated town has to offer.
Concord
If you want to soak in the New England spirit that Massachusetts is known for, then travel 20 miles from Boston and into the historic town of Concord. Once called “Nashawtuc” or “between the rivers” by the various Nipmuc groups of the native Massachusetts tribe, Concord was forever scarred in 1775 by the first battle of the American Revolutionary War.
Aside from a war for independence, Concord is also visited due to the Sleepy Hollow Cemetery, where American paragons like Louisa May Alcott, Nathaniel Hawthorne, Henry David Thoreau, and Ralph Waldo Emerson are interred for their contributions to Transcendentalism. The minuteman statue at Concord’s Old North Bridge was fashioned by Daniel Chester French, the same artist who sculpted Abraham Lincoln at the Lincoln Memorial in Washington D.C. Consider staying at Concord’s Colonial Inn, North Bridge Inn, and Residence Inn.
Lenox
The Berkshires is home to many hidden and gem-precious towns. Lenox (the town of Lenox, not the company also called Lenox) is one of the most underrated and out-of-the-way small towns in the beautiful Massachusetts hills. There, you will uncover the sublime Tanglewood, the summertime retreat of the Boston Symphony Orchestra. There, you will enjoy the garden home called The Mount, where Pulitzer-prize winning author Edith Wharton—famous for her novel The Age of Innocence—once resided. And there, you will be astounded by the Pleasant Valley Wildlife Sanctuary, a perfect paradise for birdwatching and nature trails. More wondrous delights await at Lenox, especially unparalleled establishments like the Apple Tree Inn, Brook Farm Inn, and The Whitlock.
Northampton
People who visit Northampton can appreciate why it is called “Paradise City.” The town, only about 25 minutes from Springfield, is centrally located near the Connecticut River, Mount Holyoke, and Mount Tom Ranges. Originally called Nonotuck (Algonquian meaning “middle of the river”), Northampton was unfortunately in the middle of King Philip’s War in 1675–1676 and Queen Anne’s War in 1702–1713.
At the David Ruggles Center, visitors can appreciate Northampton’s overlooked appearance as it was the perfect hiding place for free-thinking abolitionists like Sojourner Truth, William Lloyd Garrison, David Ruggles, and Frederick Douglass. Though it is an underrated town, it was the loving home to former US president and mayor of Northampton, Calvin Coolidge. If you require a good place to spend the night, the Hotel Northampton has the right services for you.
Westford
With its rolling hills, sparkling lakes, and scrumptious apple orchards, the small town of Westford captures the simplicity that Massachusetts is loved for. As unassuming as this town might be, there are many admirable and delightful amenities that travelers all over will enjoy. For example, you can pluck and sample Westford’s pristine natural produce during the Apple Blossom Festival in May and the Strawberry Festival in June.
As you travel through the vibrant streets, take a detour to meet the formidable Westford Knight, a mysterious stone carving thought to be a medieval effigy. Afterwards, play around at the Nashoba Valley Ski area for snowboarding adventures. Once all the excitement gets you weary, relax at the Westford Regency Inn and Conference Center.
Sandwich
Take a grateful bite at Sandwich, one of the oldest towns in Cape Cod and the whole of the US since 1639. 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 outdoorsperson. With a New England charm and dazzling aquatic attractions like the Scusset Beach State Reservation or Springhill Beach, Sandwich is definitely a snack worth savoring. Believe in the town’s motto, Post tot Naufracia Portus, which means "after so many shipwrecks, a haven.” Find your much-needed haven at The Dan’l Webster Inn & Spa or Sandwich Lodge & Resort.
North Adams
In the northwest corner of Massachusetts, near the border states of New Hampshire and New York, the town of North Adams is a dynamic dwelling with a deep history. The Hoosac Tunnel, a historic railroad that runs underneath the Hoosac Mountain and connects Northern Berkshire towns to Florida, emphasizes the town’s vital role in transportation. The North Adam Museum of History and Science further illustrates the town’s background. One can brave the Mount Greylock State Reservation, where the highest peak in Massachusetts beckons adventurers with spectacular panoramas of the land.
Meanwhile, the Windsor Lake and the cascading Windsor Dam lulls tourists with its relaxing waters. In mid-September, the Massachusetts Museum of Contemporary Art (MASS MoCA) hosts the annual FreshGrass Festival, where visitors are treated to bluegrass music and other stunning performances. Lest you forget, book rooms at The Porches Inn at MASS MoCA.
Hudson
Hudson, approximately 17 miles from Worcester, is a serene village along the Assabet River. As a town steepled in history, the Felton-Smith Historic Site enlightens travelers about Hudson’s industrial past and its contributions during the Revolutionary War and the American Civil War. The Assabet Woolen Mill and the Hudson Armory are architectural relics of those arduous times, though the latter now functions as an arts and culture center. The American Heritage Museum also serves as a helpful educational nexus, and it neighbors splendidly beside Marlborough-Sudbury State Forest, where you can take scenic strolls through Massachusetts wild woods. The Danforth Falls Conservation Area and the Assabet River Rail Trail provide more opportunities for gorgeous exploration.
Amesbury
Lounging on the placid Merrimack and Powwow Rivers, the town of Amesbury suffered an unfortunate episode of witch hysteria in the 1600s. Because of its close proximity to Salem (about 40 minutes away), many women in Amesbury endured similar discrimination from their peers and neighbors—although there are no documented records or landmarks confirming who endured the worst. Regardless of this morbid and sordid past, Amesbury now shines as a beacon of tranquility which abolitionist poet John Greenleaf Whittier often described affectionately in his poems. One can visit Lowell's Boat Shop, the oldest continuously operating boat shop in the US and a testament to the town’s shipbuilding history. The Amesbury Carriage Museum, likewise, elaborates on the town’s carriage manufacturing operations throughout the state.
Provincetown
Most people assume that the Pilgrims from The Mayflower first landed in Plymouth in 1620. In actuality, they made a quick stop at Provincetown around the same time. Located at the northernmost tip of Cape Cod, Provincetown educates travelers about the facts of the historic visit at the Pilgrim Monument and the Provincetown Museum. In addition to be an ignored landing site for the Pilgrims, Provincetown is a proud safe haven for members of the LGBTQ+ community. As a result, the Provincetown Art Association and Museum showcases bohemian art exhibits and modernist displays for everyone. So explore this region where the Wampanoag and Nauset tribes once roamed, and spend your moments in fine lodgings like Admiral’s Landing, Ainsworth Cottages, and Anchor Inn Beach House.
Newburyport
About 35 miles north of Boston, the seaside town of Newburyport is anchored in rich maritime traditions and natural appeal. Located where the Merrimack River floods out into the Atlantic Ocean, Newburyport has several enchanting attractions that you will enjoy. Soak in the sun and the fun at the barrier island of Plum Island, or while exploring the historic Plum Island Lighthouse and Newburyport Harbor Light. Stroll through Spencer-Peirce-Little Farm, a historic property that takes travelers back to agricultural life in the 1690s. Attend the Topsfield Fair, America’s oldest country fair since 1818, which runs from September 29 through October 9. Or perhaps attend the Yankee Homecoming event—an annual celebration founded by local artist Jack Frost to cement the bonds between New England communities, which begins from July 27 to August 4. Last but not least, recharge and refresh at Compass Rose Inn, Clark Courier Inn, or Garrison Inn Boutique Hotel.
Rockport
Rockport, about 30 minutes from the bewitching town of Salem, is a splendid epitome of a seaside town. The silver waves of Cape Ann kiss a number of shorelines like the Front, Back, Garden, and Pebble beaches of Rockport. This overlooked village also has a triumvirate of historic lighthouses that have guided ships to these majestic shores. The Thacher Island Twin Lighthouses, for example, is the only lighthouse with fully operational multiple lights on the East Coast of the US. People who have visited Rockport laud the thirty or so art galleries at the Rockport Art Association and Museum, a testament to Rockport’s status as one of the oldest art colonies in America. Rockport not shy of having pristine accommodations by the sea, and the Lighthouse Lane Cottages, Rockport Inn & Suites, and The Emerson Inn by the Sea are a handful of domiciles you can opt to stay.
In Conclusion
The best treasures are the ones few people rarely find, and the best paths are the roads less traveled. Massachusetts, meaning “near the great hill,” has some of the most underrated towns that one ought to visit due to the secrets and charms awaiting there. Feel liberal and merry in Provincetown’s, a haven for the LGTBQ+ community. Immerse yourself in America’s brutal past in Concord or Hudson. And savor the quaint delights of Westford. Massachusetts’s overlooked villages have as much cultural and natural wonders to offer as Quincy, Boston, and Harvard. Give yourself an adventure near the great hill.
