7 Massachusetts Towns Where Time Stands Still
With an impressive list of firsts, Massachusetts is a state oozing history. It is one of America's original thirteen colonies and is considered the birthplace of the American Revolution. The state is no stranger to notoriety, from witch trials to pirates, while offering inspiration for American icons like Norman Rockwell. Much of this history is so carefully preserved, one might be fooled into thinking they have stepped back in time.
From the seaside villages along the coast to the peaceful towns in the Berkshires, here are seven Massachusetts towns where time stands still.
Stockbridge
European settlement began in Stockbridge in the late 1730s with the arrival of John Sergeant and the establishment of a mission. The town’s economy relied on manufacturing in the 19th century until its idyllic location in the Berkshires launched its tourist industry.
To say Stockbridge is an image right out of a Norman Rockwell painting is no exaggeration. The iconic American artist captured the town he called home for 25 years in his work, Home for Christmas. You can view the painting at The Norman Rockwell Museum in town.
Those same streets take you back to simpler times in what is literally a picture-perfect downtown. Little boutiques and eateries line Main Street or sit tucked away in The Mews. Specialty shops like Peace, Love & Chocolate indulge your latest craving, whether it is gelato and soda floats in the summer, a warming espresso sipped on a comfy couch in the fall, or elegant truffles for the holidays.
Guided tours of the Colonial-era Mission House weave the town’s intricate story from the perspective of both the Mohicans and colonists, while Chesterwood takes you into the elegant days of the early 1900s. Rockwell was not the only artist attracted to the serenity of the Berkshires. Daniel Chester French, America’s most renowned sculptor, built the impressive three-floor estate in 1901. The charming mansion is surrounded by stunning grounds woven with hiking trails, and visitors can tour the studio, view his impressive art collection, and, of course, explore the immaculate residence.
Rockport
Situated on the northeast tip of Cape Ann, Rockport is a coastal town originally settled as a fishing village in the late 17th century. Today, the well-preserved maritime heritage harkens back to the early days of fishermen heading out to sea from the shacks at Bradley Wharf. Quirky and colorful Bearskin Neck is filled with shops, galleries, and eateries where you can explore the historic wharves and take in the ocean views. The rickety, pedestrian-friendly area feels like a movie set with its painted clapboard façades, weather-worn shacks, and cedar shingles.
Pop into shops like the family-owned Bearskin Neck Country Store, where an eclectic mix of retro candies, gifts, and souvenirs make for fun discoveries. The shop also has a player piano and penny press to complete its vintage vibe. Browse the work at galleries like the Art Nook to find original paintings and prints, or wander over to Dock Square, where the shelves at Lulu’s Pantry are stocked with enticing foodie delights.
Gobble down stellar seafood at The Lobster Pool Restaurant, deemed Yankee Magazine’s “Best Lobster with a Sunset and Ocean View.” They aren't wrong. This casual shack is self-serve only with gob-smacking views of Ipswich Bay and the coasts of New Hampshire and Maine in the distance. But the seafood just might outshine that view with fresher-than-fresh hot boiled lobsters, steamed clams, homemade chowder, and a where-have-you-been-all-my-life lobster roll.
Salem
Historic Salem sits on the North Shore of Greater Boston, where the notorious Salem Witch Trials took place over three centuries ago. Despite never outliving its infamy, the town is all charm and quaintness with its mix of painted clapboard buildings, cobblestone sidewalks, and colonial brick-front homes. Just the right touch of gothic churches adds to the town’s witchy heritage.
All that's missing when strolling the cobblestone streets at the Essex Pedestrian Mall is the clip-clop of horses. While the witch theme can feel a little overwhelming here, you can escape the touristy trap feel at Gulu Gulu Café. Although the café is more boho than witchy, the mix of artisan sandwiches, craft beer, and featured artwork is magical.
Despite the fact that the McIntire Historic District walking tour starts at the Witch House, this tour is all about the diverse architecture of Salem. The residential area is named after Salem’s most notable architect, Samual McEntire and encompasses several notable eras, from the homes of sea captains to modest cottages built between the 1640s and 1940s. McEntire’s work includes the Peirce-Nichols House and Hamilton Hall, which are open for tours.
Get caught up in the intrigue of Salem’s pirate past at Real Pirates, where the infamous “Black Sam” Bellamy comes to life through stories and immersive displays. Find out why he was dubbed the Prince of Pirates, meet his love, the “Witch of Wellfleet,” and learn how he became the richest pirate on the high seas.
Sandwich
Situated on the northwest corner of Cape Cod, Sandwich was founded in 1637 by Edmund Freeman. The original settlers consisted of just 60 families attracted to the ample salt hay for livestock feed and relief from the strict beliefs of the Puritans in the Colony. As the oldest town on Cape Cod, Sandwich is 100% New England, from its sweeping beaches to its historic homes and its artisans to its weather-worn cedar shingles. A walk along Grove Street marks some of the town’s oldest homes, dating as far back as the late 1630s. The circa 1675 Hoxie House Museum is believed to be the oldest classic Saltbox house on Cape Cod and Cape Cod’s oldest home open to the public.
The charming little home sits on a bluff overlooking Shawme Pond, where the Dexter Grist Mill has operated since 1640. When open for tours, you can take home a bag of fresh-milled cornmeal. Surrounded by colonial homes and the Town Hall, the pond is an idyllic spot frozen in time.
Glassware contributed to Sandwich’s economy in the early nineteenth century. The Sandwich Glass Museum celebrates over 200 years of glassmaking in the town, and you can watch artisans transform glowing balls of molten glass into stunning pieces of art or purchase handcrafted glasswork at the shop.
Marbleheadv
Marblehead sits on a peninsula on the North Shore overlooking Massachusetts Bay. Although deemed the “disputed” Birthplace of the American Navy, Washington did commission the founder of the Marblehead Militia to arm merchant vessels in town and later build several naval vessels to fight the British. The pre-Revolutionary buildings are a testament to the fishing village’s prosperous past. Take a walking tour of the town’s historic district to explore grand Georgian houses graced with gables, elegant columns, and double chimneys. Discover the churches, charming squares, and wharves of the historic streetscapes.
The stately Jeremiah Lee Mansion sits almost untouched from its original design created for Massachusetts’s wealthiest merchant and ship owner in 1768. Seasonal tours of the interior include a rare look at hand-painted 18th-century English wallpapers where they were originally hung, along with excellent examples of early American furniture and décor from the 18th and 19th centuries.
See America’s most iconic painting, The Spirit of ’76, painted by Archibald M. Willard at historic Abbot Hall, where you can also visit the main floor Maritime Museum. The building’s ornate clock tower and red brick façade have overlooked the town since 1877. If you need a break from human settlement, grab your binoculars and follow the trails at Marblehead Neck Wildlife Sanctuary to search the trees for birds stopping along their migratory paths in the spring and fall.
Newburyport
European immigrants settled at the mouth of the Merrimack River in the 1630s, establishing the site that became the flourishing fishing, shipping, and shipbuilding town of Newburyport by the 1730s. The town has reinvented itself several times since a fire in 1811 as the first major commercial port on the eastern seacoast and birthplace of the U.S. Coast Guard.
Newburyport’s Market Square Historic District preserves the Federalist-era architecture and charming red brick of the town's post-fire buildings. Visit the district's Custom House Maritime Museum to browse the community gallery exhibits representing different periods of Newburyport’s maritime history.
Two restored historic mill buildings are at the heart of Merrimac Street’s Tannery Marketplace, where you can window shop or discover tempting eateries and cheerful spots serving libations. You can also visit on a Sunday to stroll the stalls at the weekly farmer’s market for fresh produce, wine, cheese, and handcrafted jewelry and art.
Take the bridge to Plum Island to explore the trails, laze on the beach, and visit the lighthouse. Built in 1898, Plum Island Lighthouse guided ships navigating the treacherous waters at the mouth of the Merrimack River.
Great Barrington
Although more than a dozen fires tried to wipe Great Barrington off the map, the charming town still sits in its peaceful spot in The Berkshires on the Housatonic. Founded in 1761, the town served a role in the Revolutionary War and prospered from a strong manufacturing economy fed by The Berkshire Railway.
The historic buildings that survived the many fires or sprouted up as part of the town’s rebuilding efforts sit along Railroad Street and the small but sweet downtown’s Main Street. Elegant brick façades topped with ornate cornices line the streets where you can discover hidden alleys and browse an assortment of galleries. The Iris Gallery of Fine Art’s collection of contemporary works by local artists includes photography, painting, and mixed media displayed in a light and airy space.
The Queen Anne-style mansion, Wainwright Hall, was built in 1766 by Captain Peter Ingersoll and now serves as the Wainwright Bed & Breakfast, where guests can relax on the shaded porches or sleep beneath its charming gabled roofs. A walking tour in the town’s historic district takes you to buildings from the 18th and 19th centuries, including the Congregational Church & Manse. Built in the early 1880s, the Manse features Romanesque-revival details, a striking stone façade, and a dramatic arched entry. The Victorian Gothic stylings of the church’s bell tower are balanced by a large circular stained-glass window set above the entry.
Stop in for libations at MoonCloud to rediscover the beauty of a well-made cocktail in a cozy, intimate space while nibbling a thoughtfully prepared Tagliere Board.
Whether you visit the Main Street immortalized by Norman Rockwell in Stockbridge, explore the birthplace of the American Navy in Marblehead, or discover Cape Cod's oldest town, time stands still in these historic Massachusetts towns. So put on your comfy traveling clothes and set your nav system to find one of the many New England towns frozen in time.
