11 Most Laid-Back Small Towns in Massachusetts
Transcendentalism, one of the first philosophical to come out of the US, was born in New England. Can you guess what its birthplace was? Here’s a hint: It isn’t Boston! When most people think of the Commonwealth of Massachusetts, large, well-known cities like Boston and Salem immediately spring to mind. But the Bay State also offers a wealth of inviting small towns chock-full of history for those yearning for a change of pace and scenery. From the beautiful trails of Weston and cultural sites in Lenox to the irresistible charm of Nantucket, below are eleven small towns you should definitely pencil into your itinerary the next time you visit marvelous Massachusetts.
Rockport
Set just 40 miles north of Boston in Essex County, Rockport is a seaside village revered for rocky trails winding through woods and meadows and pleasant miles of coastline. Let your worries melt away by sunbathing with a drink in hand at Front Beach or Back Beach. Sample fresh, local seafood at one of many casual and fine dining restaurants after browsing unique shops on Main Street. Art lovers rejoice: Rockport’s art colony, one of the oldest in America, features more than thirty galleries as well as the Rockport Art Association and Museum. A host of year-round community events, from Harvest Fest to Christmas in Rockport, are sure to immerse you in endless fun. What’s more, your choice of accommodations ranges from historic New England inns and B&Bs to fantastic hotels offering all manner of modern amenities.
Lenox
Incorporated in 1767, the town of Lenox, Massachusetts, is situated in lovely Berkshire County. Each season attracts thousands to the Berkshires for its splendid scenery, vibrant arts scene, and engaging activities. Originally a town of traders, merchants, innkeepers, and farmers, Lenox participated in the Revolutionary War, contributing soldiers and support to the Patriot cause. In the 19th century, the well-heeled residents of Boston and New York were captivated by the scenic fields and forests of the Berkshire Hills, which reminded them of those in Switzerland.
Two Gilded Age cottages in Lenox are open for public tours: Ventfort Hall, the grand 1893 summer home built for George and Sarah Morgan, sister of J.P. Morgan, and The Mount, the 1902 home designed and owned by author Edith Wharton. Both sites are listed on the National Register of Historic Places. Want a little break from all the history? Explore diverse plant collections at the Berkshire Botanical Garden, enjoy shopping and dining at Lenox Village, or catch a performance at Shakespeare & Company.
Provincetown
Gracing the northern tip of Cape Cod, this seaside town is on the site of the Mayflower’s landing in 1620, commemorated by the 252-foot Pilgrim Monument, where you can get a bird-eye view of the whole town and adjacent Provincetown Museum. Various restaurants, galleries, shops, and nightclubs are clustered on and around lively Commercial Street. Boasting forty miles of picturesque beaches, it’s no wonder Provincetown has frequently been recognized as a top beach destination, one of the best small towns in America by various travel publications.
Take a dip at Race Point Beach or Herring Cove Beach, go whale watching, check out nature preserves and scenic trails, or tour the Norman Mailer Center, which honors the life and work of the acclaimed author. Popular historic landmarks, including Town Hall, the Art House, and the Crown & Anchor, are beckoning to be explored. Alternatively, you can soak up spectacular views at the historic Race Point Lighthouse or Macmillan Pier, one of the world’s natural deep-water harbors.
Great Barrington
Named after the village of Great Barrington in Gloucestershire, England, the village of Great Barrington was first settled by colonists in 1726. In the summer of 1774, 1,500 men shut down the Berkshire County Court in response to British oppression. In the winter of 1776, Henry Knox, George Washington’s future Secretary of War, passed through Great Barrington while transporting cannon from Fort Ticonderoga to the Siege of Boston.
The colonial home of the poet William Cullen Bryant (who was town clerk between 1815 and 1825), as well as the houses of Colonel Ashley and Henderson, are preserved in Great Barrington. In addition, not only was the noted author and sociologist W.E.B. Du Bois born in the town, but the world’s first alternating current with transformer system was conceived here. You can browse the shops at Main Street, enjoy a picnic at Lake Mansfield, or try one of the town’s popular farm-to-table restaurants and coffee shops.
Nantucket
Thirty miles off the south coast of Cape Cod, this island community’s fine dining establishments, cobblestone streets, charming inns, and elegant hotels draw hordes of visitors year-round. From fascinating museums and eclectic museums to a beautiful harbor, there’s plenty to do and see. Those interested in working on their tan or simply unwinding to stellar ocean views will appreciate 82 miles of pristine beaches, while adventurers can avail of an extensive network of hiking trails and bicycle paths.
In 1602, an Englishman named Bartholomew Gosnold first spotted the island; though the island had long been known to Indigenous peoples, it wasn’t settled until 1659. Over time, Nantucket has evolved from one of North America’s premier whaling ports to a tourism mecca. From the Brant Point Lighthouse to Siasconset Village and Coskata-Coatue Wildlife Refuge, there’s no shortage of picturesque spots from which to take a few selfies with friends or create special memories with family.
Chatham
This rich history of this seaside town at the southeastern tip of Cape Cod has a rich history stretching all the way back to 1606, when Samuel de Champlain is known to have explored the area and encountered the Monomoyiks, a Native American tribe numbering between 500 and 600 members. Though Chatham struggled to establish a stable footing in its first 100 years, the town finally did so after the Revolutionary War, as industries like shipbuilding, salt production, and fish export brought the local economy to life.
Today, the town continues to prosper thanks largely to its wealth of shops and restaurants and popular beaches, which attract tourists, summer residents, and retirees alike. Be sure to take in spectacular views at the Chatham Lighthouse, which was established in 1808 and is one of the few remaining lighthouses in America to operate 24 hours a day.
Concord
Concord is the answer to the question posed at the outset. Indeed, the transcendentalist movement owes its origins to this cultural hub that literary luminaries like Ralph Waldo Emerson, Henry David Thoreau, Nathaniel Hawthorne, and Louisa May Alcott called home. Roughly a half-century before this, however, Concord shares with Lexington the distinction of marking the start of hostilities in the American Revolutionary War. The town features the North Bridge, where the famous Shot Heard 'Round the World was fired.
History buffs won’t want to miss Minute Man National Historical Park, which includes the reconstructed North Bridge and Daniel Chester French’s renowned bronze Minuteman Statue; and the Concord Museum, which showcases relics of the Revolution, the contents of Emerson’s study, and a collection of Thoreau’s belongings. What’s more, you can visit the homes of Emerson, Hawthorne, and the Alcotts, along with Walden Pond State Reservation, where you can see the site of Thoreau’s original cabin. Beyond immersing yourself in history, you can take a leisurely stroll through the Concord River Greenway, go kayaking on the Concord River, or dine at one of many outstanding restaurants, like 80 Thoreau.
Stockbridge
Speaking of Nathaniel Hawthorne, the author composed The House of Seven Gables in a small red cottage in Stockbridge, just south of Lenox. It is here you’ll also find the Norman Rockwell Museum, featuring the largest collection of the artist’s work. Stockbridge was incorporated in 1739 and has been an important cultural, artistic, and intellectual center since. Like many towns in colonial New England, its own militia participated in the Revolutionary War, and Stockbridge also aided in the war effort by providing funding, supplies, and other types of assistance.
Be transported back to the Gilded Age at the Naumkeag House and Gardens, catch up on your reading at the Stockbridge Library, and soak up enthralling performances at the nearby Mahaiwe Performing Arts Center. You’ll marvel at the festive lights of Stockbridge Main Street at Christmas, a can’t-miss event for people of all ages.
Orleans
Situated along Cape Cod in Barnstable County is this lovely town of roughly 6,500 residents. Beachgoers can enjoy great surf at Nauset Beach, while outdoor enthusiasts can walk or bike along the expansive Cape Cod Rail Trail. You can learn about the history of Orleans and Cape Cod through wide-ranging artifacts and exhibits at the Orleans Historical Society Museum. If time allows, treat yourself to whale or seal watching on a scenic boat tour.
It might strike you as odd that a town in Massachusetts would have a French name. As it turns out, the town was named in honor of Louis Philippe II, Duke of Orléans, to recognize France's support of the American cause during the American Revolution. Looking to commune with nature? Check out the Monomoy National Wildlife Refuge, known for its diverse bird species, or simply unwind at the Orleans Waterfront. And whether you’re a golf novice or a pro, you can tee off at any of several golf courses.
Weston
Situated roughly 15 miles west of Boston in Middlesex County, Weston is steeped in abiding historical charm. It has gradually evolved from a rural farming community during the 17th and 18th centuries into an affluent town characterized by historic architecture, a quaint atmosphere, and verdant spaces. The Golden Ball Tavern Museum, originally a site for meetings amongst Loyalists during the American Revolution, dates back to 1770 and displays neat artifacts from the American Revolution and 1800s, including artworks and teapots.
Just on the northern tip of Weston, Silver Hill is a historic district recognized for its Queen Anne- and Colonial-style homes. The homes feature open front porches, wood frames, and landscapes with stone walls similar to those common in the 18th century. Not to be missed are fabulous restaurants like Theo’s Pizzeria and Dumpling Daughter. The area's downtown underwent an $18-million revitalization in 2022, enhancing the town center's function, appearance, and safety. Learn more about the area’s rich history at the Weston Historical Society before enjoying a relaxing stroll along the Weston Town Green.
Duxbury
The seaside town of Duxbury is roughly 35 miles southeast of Boston. Extending six miles from Marshfield to the Plymouth villages of Gurnet Point and Saquish, Duxbury Beach makes an ideal spot for paddling, swimming, and sunbathing. Get your local history and culture fix at the Duxbury Rural and Historical Society. While you’re at it, be sure to visit the Alden House, the 17th-century family homestead of Mayflower passengers John and Priscilla Alden and their descendants.
The King Caesar House is a federal mansion built in 1809 for Ezra Weston II, known as "King Caesar" for his worldwide acclaim as a merchant and shipbuilder. Stroll through Myles Standish State Forest to observe wildlife before stopping for a relaxing picnic. Other highlights include a free library, dining, and various community events throughout the year.
Experience the Charm of Massachusetts' Small Towns
As you can see, the state of Massachusetts provides a treasure trove of laid-back small towns that are less densely populated than cities like Boston but no less charming - making for the perfect romantic escape or family vacation. Whether you want to browse the art galleries of Rockport or sunbathe on a windswept beach in Provincetown, there’s something for everyone to enjoy. Who says that you always have to venture to a bustling metropolis in order to have a good time?
