10 Coziest Towns to Visit in Massachusetts in 2024

Massachusetts was where three of the first historic events transpired in American history, these being the first telephone call, the establishment of the first American railroad, and the first battles of the American Revolutionary War. But for travelers such as yourselves, Massachusetts can be the first state to visit when exploring the coziest small towns this 2024. Beyond the illustrious confines of Harvard and the busy streets of Boston, you will be mesmerized by Northampton’s historic battlefields, Amesbury’s mirroring of the Salem Witch Trials, and Provincetown’s liberal attitudes. So get comfortable as you venture into the coziest towns to visit in Massachusetts in 2024.

Rockport

Approximately 30 minutes from the infamous town of Salem lies the sunny, seaside town of Rockport. Beachgoers can soak in the Atlantic Ocean from the shorelines of Cape Ann, notably from Front Beach, Back Beach, Garden Beach, and Pebble Beach. For a grand view of Rockport and its splendid surroundings, you can stand atop one of three historic lighthouses in town, the best being the Thacher Island Twin Lighthouses as it is the only lighthouse with fully operational multiple lights on the East Coast of the US. At the Rockport Art Association and Museum, over 30 or more art galleries showcase some of the best artworks and masterpieces from the oldest art colony in America. No need to worry about lodgings since the Lighthouse Lane Cottages, Rockport Inn & Suites, and The Emerson Inn by the Sea are suitable spots for you to feel right at home in Rockport.

Northampton

Live a paradise on earth in Northampton, “Paradise City.” Approximately 25 minutes from Springfield, Northampton was originally called Nonotuck, an Algonquin word for “middle of the river” as a reference to its location near the Connecticut River. From the summits of Mount Holyoke and Mount Tom Ranges, you can get a great view of the lay of the land which was endured the hardships of King Philip’s War in 1675-1676 and Queen Anne’s War in 1702-1713. In later years, Northampton was known for being a hiding spot for abolitionists such as Sojourner Truth, David Ruggles, Frederick Douglass, and William Lloyd Garrison. Their struggles and that of other abolitionists can be reviewed at the David Ruggles Center, just as Calvin Coolidge Presidential Library and Museum showcases the life and times of President Calvin Coolidge. When it comes to lodgings, the Hotel Northampton does not disappoint.

Concord

Concord, originally called “Nashawtuc” or “between the rivers” by the Nipmuc groups of the native Massachusetts tribe, is one of the oldest towns in Massachusetts. Only about 20 miles from the city of Boston, Concord is notable for being the resting place of Louisa May Alcott, Nathaniel Hawthorne, Henry David Thoreau, Ralph Waldo Emerson, and other American Transcendentalists at the Sleepy Hollow Cemetery.

Most importantly, Concord is one of the first battlefields that initiated the American Civil War in the year 1775. More history can be gleaned via renowned artist Daniel Chester French—the same man who sculpted the Abraham Lincoln Statue at the Lincoln Memorial. His masterwork in Concord, the minuteman statue at Concord’s Old North Bridge, continues to welcome newcomers. If you are intrigued to see more of Concord’s attractions, then you should definitely book a room at either the Concord’s Colonial Inn, North Bridge Inn, or Residence Inn.

Westford

Westford is the kind of town that many who desire the clean, perfect, serene lifestyle will fall in love with. Dozens of superb lakes and lush hills surround this majestic town, and every year the townsfolk celebrate the Apple Blossom Festival in May and the Strawberry Festival in June. The Westford Knight, an enigmatic stone carving believed to be a medieval effigy, stand sentinel in Westford’s town square. Although Westford is certainly a green and lively town, come winter the snow creates excellent opportunities for skiing at the Nashoba Valley Ski. There is no shortage of fun and adventures to be savored in Westford, but should you grow weary and exhausted from such exhilarating thrills, you can always refreshen at the Westford Regency Inn and Conference Center.

Provincetown

Make a pilgrimage to the actual place that the Pilgrims of The Mayflower landed at in 1620—Provincetown, a community which the Wampanoag and Nauset tribes once settled before immigrants from Europe established more permanent residences in Cape Cod. One can learn the truth of this fact at the Pilgrim Monument and the Provincetown Museum while also learning more about the diverse communities in Cape Cod. Meanwhile, the Provincetown Art Association and Museum embodies the LGBTQ++ community Provincetown supports, best seen in the numerous bohemian artworks on display. Should you wish to see more of Provincetown’s inclusive and diverse atmospheres, then store your belongings at the Admiral’s Landing, Ainsworth Cottages, or Anchor Inn Beach House.

North Adams

North Adams, situated near the state border between New Hampshire and New York, is a riveting small town replete with some of the best modern attractions in Massachusetts. From the North Adam Museum of History and Science which emphasizes the importance of science and history to the Mount Greylock State Reservation—the highest peak in Massachusetts—these destinations will engage your mind and muscle. Even visitors from Florida can visit North Adams thanks to the Hoosac Tunnel, connecting towns from Northern Berkshire to Florida via routes beneath the Hoosac Mountain. More exploration beckons from the Windsor Lake and Windsor Dam, and every year in mid-September, the Massachusetts Museum of Contemporary Art (MASS MoCA) celebrates the FreshGrass Festival for bluegrass music and other festivities. For accommodations, look no further than to The Porches Inn at MASS MoCA.

Lenox

Deep in the hilly regions of the Berkshires idles the humble and laidback town of Lenox. From a garden residence called The Mount, you will come upon the home of Edith Wharton, a Pulitzer-prize winning author renowned for her novel The Age of Innocence. From the summertime dwellings of Tanglewood, you will find the vacation retreats and domiciles of the Boston Symphony Orchestra whenever they need a break from their work. Last but not least, from the Pleasant Valley Wildlife Sanctuary, you will find all manner of birds and wildlife deep in the splendorous hills of Massachusetts. Come explore more of what Lenox has to offer, and seek your daily and nightly accommodations at the Apple Tree Inn, Brook Farm Inn, or The Whitlock.

Hudson

Situated on the Assabet River, Hudson has made numerous contributions to the American Revolutionary War and Civil War. It was the Assabet Woolen Mill and the Hudson Armory that American soldiers armed and clothed themselves for battle—the Hudson Armory, in particular, now serves as an arts and culture center for those eager to see Massachusetts’ aesthetic side. The Felton-Smith Historic Site further elaborates on the many conflicts Hudson witnessed, whereas the American Heritage Museum highlights Hudson’s humble beginnings. Travelers can go strolling through the Marlborough-Sudbury State Forest, the Danforth Falls Conservation Area, and the Assabet River Rail Trail for the scenery and the sensation of being in the lovely outdoors. Do not miss out on an opportunity of a lifetime by experiencing more of Hudson’s cozy charm.

Newburyport

In the banks of the Merrimack River floods lies the quaint port town of Newburyport. Whether you are traipsing through the barrier island of Plum Island or attending Topsfield Fair—the oldest county fair in America since 1818 and occurring in the period of September 29 through October 9—Newburyport’s riveting attractions will keep you coming back for more. Standing atop Plum Island Lighthouse and Newburyport Harbor Light, you can get a great view of the Atlantic Ocean. You can be thrust back into the 1690s when gallivanting through the historic Spencer-Peirce-Little Farm. A second event worth seeing in Newburyport is the Yankee Homecoming event, beginning from July 27 to August 4. Only about 35 miles north of Boston, allow the rejuvenating accommodations of the Compass Rose Inn, Clark Courier Inn, and Garrison Inn Boutique Hotel fill you with more vigor to continue your adventure through Newburyport.

Amesbury

Amesbury, located near the Powwow River and Merrimack River, bore a similarly misfortunate history to Salem which is about 30 miles away. In the hectic and hysterical 1600s, Amesbury’s townsfolk condemned many of its women and even male peers to the same witch trials of the times. However, there are currently no documented records or landmarks identifying the victims of this medieval discrimination. Fortunately, Amesbury has since progressed from such a sordid past. Even abolitionist poet John Greenleaf Whittier described Amesbury with love and attention. Whether you are taking a sailing trip from Lowell's Boat Shop—the oldest continuously operating boat shop in the US—or reviewing Amesbury’s carriages at the Amesbury Carriage Museum, there are plenty of newfound wonders and delights to enjoy in Amesbury.

The name Massachusetts comes from the Massachusetts tribe which in turn means “at or about the Great Hill”—most likely an allusion to the Berkshires. It is within this state of firsts that one will find some of the most liberal, jovial, and coziest towns to visit this 2024. There is an openness and inclusion for the LGTBQ+ community to be enjoyed in Provincetown. There is history and wonderment to be studied in Concord and Northampton. There are festivities aplenty in Westford, and simple luxuries in Lenox and Rockport. But most of all, there will travelers like you who will earn memorable experiences in the beautiful state of Massachusetts. Stay safe and cozy in the coziest towns to visit in Massachusetts this 2024.