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Carnival parade in Provincetown, Massachusetts. Image: Vadim 777 / Shutterstock.

9 Best Downtowns In Massachusetts

Massachusetts's nickname, "Old Bay State," accurately describes the state's maritime heritage. It is not just a sprawling concrete jungle, as many may envision when associating Massachusetts with Boston. Rather, Massachusetts is a hub of education and art with a rich background in American history set against the backdrop of the sea. These 9 best downtowns are filled with intriguing tales, like the infamous Salem witch trials, delicious meals at rustic locations like Turner’s Seafood, and charming coastal landmarks, including the famous Walden Pond. Visitors will get more than expected in these historic and beautiful little downtowns.

Northampton

Northampton, Massachusets
View of buildings in downtown Northampton, Massachusetts, home to Smith College. Image: EQRoy / Shutterstock.

Northampton, in central Massachusetts, is a compact blend of entertainment and culture with more art galleries and theaters than you'd expect from a smaller town. The Academy of Music Theatre, which shows both movies and live performances, opened in 1891 and is the first city-owned theatre in the country. After a show here, you can catch another at the Northampton Center for the Arts or live music at The Iron Horse, The Parlor Room, or Calvin Theater.

If you enjoy a more stationary visual art experience, you can visit the Smith College Museum of Art, housing over 25,000 pieces. Before or after indulging in some art, you can stroll over to Northampton Brewery or Progression Brewing Company for a Northampton-made beer and snacks. For those looking for some American history, head over to the Calvin Coolidge Presidential Library and Museum, dedicated to the life and career of the 30th President, who spent much of his life in the city, or the Historic Northampton, a museum to the city's history.

Downtown, you can indulge in local food and shop at more than twenty businesses inside historic Thornes Marketplace. Alternatively, stroll to Northampton Brewery or Progression Brewing Company for some Northampton-made brew and bites.

Provincetown

Provincetown, Massachusetts
Aerial view of Provincetown, Massachusetts and its Pilgrim Monument.

Provincetown is a seaside arts town located at the northern tip of Cape Cod. It is a narrow, curved piece of land situated between Cape Cod Bay and the Atlantic Ocean. Due to its location, it has some of the best seafood and dining views in the northeast at iconic restaurants like Lobster Pot, Fanizzi's, and Jimmy's HideAway.

The city's history is significant. In 1620, it was the site of the Mayflower Pilgrims' first stop in the New Â鶹AV before settling on Plymouth Rock across the bay. Visit the Pilgrim Monument and the Provincetown Museum to engage in an immersive learning experience about the historic event.

Salem

Salem, Massachusetts
Overlooking downtown Salem, Massachusetts.

Salem is a coastal city brimming with dark history. The city's claim to fame is being the site of the notorious Salem witch trials. Thanks to its witchy history, downtown is packed with spooky experiences like the Salem Halloween Museum and Count Orlok’s Nightmare Gallery. History seekers brave enough can visit the still-standing Witch House, the outdoor Salem Witch Trial Memorial, and the Salem Witch Museum to discover the fascinating truth behind the unfortunate events.

Those looking to learn more about the city's other history can visit the actual House of the Seven Gables from Nathaniel Hawthorne's novel or the Salem Maritime National Historic Site. Walk through the Peabody Essex Museum to view art in the oldest continuously operating museum in the United States.

In between museums, don't forget to stop for some outstanding, authentic Turner seafood at Turner's Seafood, named 'Best of the North Shore.' Alternatively, enjoy progressive New England cuisine at the swanky Ledger housed in the former Salem Savings Bank building from 1818.

Rockport

Rockport, Massachusetts
Picturesque Rockport Harbor in Massachusetts.

Rockport is the perfect little seaside town many imagine when they think of New England for a getaway. There are varying accessible beaches downtown for those who want to pick seashells, sunbathe, or swim, including Front, Cape Hedge, and nearby Back Beach, all with ideal views of the Atlantic Ocean. The impressive Shalin Liu Performance Center's stage overlooks the ocean for a one-of-a-kind concert-going experience.

Art plays an important role in Rockport, so much so that its seaside homes, shops, and restaurants are renowned and visited for their iconic looks and colors. Rockport's Cultural District is a mile-long walkable series of art galleries, including one of the oldest art associations in the US, the Rockport Art Association and Museum.

There is plenty of great local eating along the way, such as the family-owned Roy Moore Lobster Company with its waterfront seating and fresh local seafood. For a more upscale experience, Feather & Wedge offers surf and turf with a European slant and live music on Thursdays.

Newburyport

Newburyport, Massachusetts
Market Square in Newburyport, Massachusetts. Image: Little Vignettes Photo / Shutterstock.

Newburyport is a historic seaport town with a deep maritime history. It's located about an hour north of Boston on the Merrimack River. Newburyport was once a hub for shipbuilding, fishing, shipping, and privateering because of its ideal location.

The Market Square Historic District, on the National Register of Historic Places, allows visitors to shop unique local merchants like Coastal Chic while viewing the largest collection of Federalist architecture in the US dating back to the late 1700s. While in the historic district, visit the Custom House Maritime Museum, located in an original building from 1834, to explore the city's rich water-bound history

Two of the region's top eateries are just a short walk away. Loretta offers upscale American cuisine with plenty of seafood options. Black Cow offers classic New England dishes with a waterfront view but surprises with an extensive sushi menu.

Shoppers will be just as impressed with the Tannery Marketplace, seen as "the best shopping on the North Shore". The massive location is home to over 50 local businesses, including Jabberwocky Bookshop and the Newburyport Farmer's Market.

Concord

Concord, Massachusetts
Main Street in the historic town center of Concord, Massachusetts. Image: Wangkun Jia / Shutterstock.

Concord is famous for the "shot heard 'round the Â鶹AV," which began the American Revolution. The historic downtown area celebrates American independence with landmarks such as the city's Concord Museum, Minute Man National Historical Park, and the Old North Bridge, where the "shot heard round the Â鶹AV" was fired.

Though the city may be associated with war, it's also been a hub for great American writers and thinkers. Visit the home where Louisa May Alcott wrote Little Women and the home of philosopher Ralph Waldo Emerson. Downtown's Sleepy Hollow Cemetary is home to them both, as well as author Nathaniel Hawthorne and Concord native Henry David Thoreau.

To taste the city's local flavor, visit Woods Hill Table, which offers locally sourced farm-to-table New American cuisine. For a historic dining experience, stop into Liberty at Concord's Colonial Inn, built in 1716, serving classic American cuisine like chicken pot pie and pot roast.

Great Barrington

Great Barrington, Massachusetts
Aerial view of Great Barrington, Massachusetts.

Great Barrington is located in Western Massachusetts on the Housatonic River, near the New York border. Main Street, located in the center of downtown, is the first street in the US to have electric lights. While taking in its history, shop the many niche stores and businesses along the street, like Railroad St. Collective boutique shop, Rob's Records, the Bookloft, and Happy Place Berkshires, all within walking distance.

Those looking for a taste of the New England outdoors can stroll the scenic Housatonic River Walk that borders downtown. For a break from the walking, stop in and catch a live performance or movie at the Mahaiwe Performing Arts Center, which has been running continuously since 1905.

Many of Great Barrington's best restaurants, such as Cafe Adam and Pleasant and Main, use only locally sourced ingredients. The Prairie Whale is a must-visit for its distinctive locally reclaimed wood paneling interior and local farm-to-table dishes that change seasonally. Be sure to try the more casual Baba Louie's, known for their gourmet pizza that some have called the best they've ever eaten.

Lenox

Lenox, Massachusetts
A street view of Lenox, Massachusetts. Image: Richard Cavalleri / Shutterstock.

Lenox, Massachusetts, began as a farming town but became a hub for artists and lovers of architecture. Outside downtown is Tanglewood, the summer home of the Boston Symphony Orchestra and the Shakespeare and Company performing arts theater. Visitors can walk through the Gilded Age architecture that took the city by storm in the late 1800s while taking in exhibits at the Ventford Hall Gilded Age Mansion & Museum housed in an 1893 home.

In the center of downtown, there's plenty of local flair to indulge in. On Church St, travelers can stop in for notable shopping at boutique stores like The Gifted Child and Glad Rags. Those looking for art have plenty of options, with the Tom Fiorini Sculpture Yard, The Wit Gallery, the Hado-Mark Gallery, and the Hoadley Gallery all off the same road.

Celebrating their farming roots, dining in Lenox is all about local flavor; its best restaurants, also off of Church, proudly offer diverse farm-to-table menus, such as Alta's Mediterranean cuisine, Cello's American cuisine, and Bistro Zinc's French cuisine.

Gloucester

Gloucester, Massachusetts
Humpback whale breaching on the sea near Gloucester, Massachusetts. Image: Wangkun Jia / Shutterstock.

Gloucester is a coastal town on Cape Ann. It was colonized in 1623 and is called the oldest seaport in the United States. Its seafaring roots still heavily influence the city's downtown culture, dining, and art. Seafood is a major part of life in Gloucester, and the restaurants downtown proudly serve it, including fresh catches from the harbor. Tonno offers fresh Italian seafood options, while Seaport Grille and Michael's Harborside serve seafood right on the water.

While on the water, enjoy scenic views of the cape or try a whale watching excursion at Cape Anne Whale Watch or 7 Seas Whale Watch. Stop by the iconic Gloucester Fisherman's Memorial statue dedicated to those who never returned to shore.

The Cape Anne Museum, housed in multiple historic downtown buildings, displays exhibits dedicated to the art and lives of those in the seafaring town. The Maritime Museum goes a step further and educates visitors on maritime heritage through hands-on exhibits and programs.

Final Thoughts

Massachusetts may be known for its largest city, Boston, but these smaller walkable downtowns will make any traveler realize the state's variety of culture and vast importance while still showing a good time. Those looking for a relaxing getaway wrapped up in a history lesson may just find their new favorite spot to vacation. New England is known for its food, and these downtowns offer some of the best in the region, many of which sit on historic streets or in historic buildings with original architecture within walking distance of shops selling one-of-a-kind goods. Whether you visit to see a show, learn some history, or go on a foodie tour, these downtowns are worth exploring.

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