8 Massachusetts Towns With Unforgettable Main Streets

The state of Massachusetts sits upon venerable and ancient land. Today, the towns there have unforgettable main streets that reflect the rich history of the state, with original Victorian and Colonial architecture and cobblestone or brick streets, offering picturesque glimpses into the state's storied past. The smell of salt water, red maple trees, and fresh seafood permeates the air, alongside a sense of pride and patriotism, which are staples of the Bay State. From the Portuguese culture in Provincetown to witchcraft and spooky vibes in Salem, walk down the most unforgettable main streets in the state.

Provincetown

Provincetown is a coastal city that lays claim to a prolific colonial past, and is known today for the influence of Portuguese culture and hospitality to the LGBTQ+ community. Residents and tourists alike are drawn to Commercial Street, a truly unforgettable main drag featuring Cape Cod-style homes and plenty of small stores and cafes. There are many spots to indulge in delicious seafood, but locals recommend The Lobster Pot, at 321 Commercial Street. For dessert, you cannot beat Provincetown Portuguese Bakery, which has been at 299 Commercial Street since the 1930s.

For some entertainment on the artistic side, visit The Provincetown Art Association and Museum at 460 Commercial Street, which displays works by historic and modern Provincetown-based resident artists. Equally visually stunning is the MacMillan Pier, a beautifully curated outdoor space. There you will find Provincetown Waterfront Memorial Park and MacMillan Pier Bird Watching Area, both of which are exquisite, relaxing spaces, especially in warmer months.

Hingham

The Hingham Harbor has historically been a main source of income and entertainment for residents of this port and fishing town. The downtown area, which stretches along the aptly named Main Street, is worth seeing just to admire the largely original Colonial and Late Victorian style architecture. A large section of Main Street is on the National Register of Historic Places.

For example, the 1681 Old Ship Church, which you can see at 90 Main Street, is an iconic Elizabethan Gothic building, the only one left standing in North America. The Hingham Historical Society, located at 34 Main Street, maintains the 1686 Old Ordinary, a house museum which puts early American living on display, as well as the 1665 home of Benjamin Lincoln, a celebrated Revolutionary War General who fought alongside George Washington.

To see a movie, for only $10 no less, you can head down to 65 Main Street and catch a showing at the Loring Hall Cinema, a fully operational theater in a Colonial-style building which has been there since the 1850s. Afterward, it is essential to grab a dessert at Nona's Homemade, at 19 Main Street, where you can choose from a vast menu of unique ice cream flavors and cookie sandwiches.

Nantucket

An island destination for tourists in the summer, Nantucket is also a gorgeous place year-round, boasting 1800s Greek Revival style homes lining cobblestone streets and a ton of exquisite beaches that allow public access. Although the whaling industry, which had supported most of the town's economy prior to the Great Fire of 1846, was already in decline at that time, many businesses in Nantucket chose to rebuild, and the town grew into the gorgeous retreat it is today, developing its Main Street into a genuinely unforgettable area.

The Whaling Museum, located at 13 Broad Street right downtown, is a must-see, housing rotating art exhibitions, a rooftop deck which affords visitors unparalleled views of the harbor, and an awe-inspiring, 46-foot sperm whale skeleton. On vintage cobblestone Main Street, shopping at Nantucket Looms, located at 51 Main Street, will allow you to purchase handmade textiles and other gifts.

An exquisite dining experience can be had at The Club Car on 1 Main Street, in an upscale restaurant attached to a train car with live piano playing. A post-dinner walk can be taken down the Sconset Bluff Walk, a foot path which travels down the eastern shore of the town, oddly traveling right through private backyards and leading to the beach, giving an intimate look at Nantucket from the inside.

Newburyport

Both a coastal and riverfront city, Newburyport was nearly leveled by a fire in 1811. It was rebuilt as a fishing and shipping economic center, and today it remains a thriving tourist destination for visitors looking to enjoy scenic beaches and towns in Massachusetts.

One of the buildings reanimated for modern use was the Firehouse Center for the Arts, built in 1822 as the "Market House." Today, it is used as a performance arts center hosting various musical and theater productions. Surrounding the Firehouse is the Market Square Historic District, the downtown area where many Federalist-Era buildings have been turned into shops and restaurants, including Anchor Stone Deck Pizza at 44 State Street, and The Port Tavern, an Irish-American fusion pub at 84 State Street.

For less eating and more learning, check out the Custom House Maritime Museum on 25 Water Street, where Newburyport visitors can learn about the town's claim to fame as the birthplace of the United States Coast Guard and see displays of notorious shipwrecks and model boats.

Concord

Concord was the site of the first battle of the Revolutionary War, which lasted only five minutes but echoed out as the "shot heard round the world." You can still visit the North Bridge, a replica of the historic battle site, and see its accompanying Minute Man Statue, which honors the local militia who protected Concord from the British Redcoats. For more relevant sites, Concord Walking Tours at 79 Main Street can help with that. They provide guided and mapped routes of the city, taking visitors to verified sites of Revolutionary War, literary, and black history tours.

Concord was also the home of several famous authors and poets, such as Louisa May Alcott, Henry David Thoreau, Ralph Waldo Emerson, and Nathaniel Hawthorne, and established itself as a hotspot for literary greatness. Two of those, Walden and Thoreau, have streets named after them in the city's epic downtown, alongside Main Street.

Appropriately, there is a bookstore at 65 Main Street called The Concord Bookshop, which aims to showcase local authors who are both former and current residents of the city. Another essential Concord stop is the Main Streets Market and Cafe at 42 Main Street, which has been serving locals and tourists for over 100 years, establishing itself as a staple in the town.

Gloucester

The oldest seaport in the US is located in Gloucester, whose culture is centered around the water. The town is unique for being the site of some weird lore, including a sea serpent who allegedly lives in the bay, but Gloucester these days is not creepy, and is now home to a lovely coastal downtown that is sure to draw travelers in.

There is plenty to do along Main Street, including experiencing the quintessential seaside entertainment that is whale watching. Cape Ann Whale Watch, operating out of 415 Main Street, claims to provide the largest and fastest vessel suited to this activity. The Cape Ann Museum Green (CAM) is located just down the road at 13 Poplar Street, where it hosts an art gallery with free admission. CAM also hosts free musical entertainment as well as learning-based discussions about art, culture, and local history.

You should also indulge in the freshest possible seafood and tranquil waterfront views at the Seaport Grille at 6 Rowe Square. This restaurant has been cooking up high-end American classic cuisine and surf and turf since 2009, and has two outdoor decks where you can enjoy the harbor and your dinner.

Wellesley

By the 1920s, the colonial town of Wellesley was absolutely thriving, covered in carefully planned neighborhood layouts to make it as visually appealing and functional as possible. There is a great sense of pride among the people who live there, which makes it an unforgettable stop in Massachusetts. The main gathering area, Wellesley Square, is well-groomed and teeming with activity. The square is the center of dining, socializing, and a multitude of boutiques. One such store is Wellesley Books, an independent bookstore that has been a downtown staple for over 20 years.

Right beside the town square, you can find Morton Park, a very nice recreational area that is home to the iconic Wellesley Town Hall. This architectural feat is a grand 1880s Romanesque stone building that looks like a European castle, complete with towers, turrets, complex molding, and stained glass.

Nearby, the Davis Museum at Wellesley College is a charming small gallery on the college campus displaying a notable collection of contemporary and classic artworks. Also on campus, the Wellesley College Botanic Gardens are open to the public and free to visit all spring. The garden is both educational and impressive in appearance, with more than 20 acres of outdoor gardens featuring some exotic plant species that you would be hard-pressed to find elsewhere in Massachusetts.

Salem

It should be known that there is much more to this city than just witchcraft hysteria. Salem was definitely not the safest or nicest place to be back in the 1620s. Still, it is now covered in historical sites, museums, and educational opportunities, showing that they have made a concerted effort to learn and grow from the past.

One of the easiest ways to learn all the nitty gritty details while taking a scenic ride down all the ancient streets is to book a tour on the Salem Trolley. They provide witchcraft history tours. Alternatively, you can learn about some lesser-known literary and maritime history. Salem has also proven itself to be a very artistic city. The Peabody Essex Museum is an eclectic and invigorating stop, exhibiting complex takes on New England art, culture, fashion, and history alike.

More diverse and uncommon art can be seen at the Punto Urban Art Museum, another unforgettable stop. It is a one-of-a-kind outdoor public art museum, made up of outdoor murals painted on local businesses. Afterward, a good hearty meal of ocean fare can be had at Turner's Seafood, where a lengthy menu features mostly fresh catches and other New England fare. It is also located in a historic building, Lyceum Hall, which is even said to be haunted.

Massachusetts is a great tourist destination for so many reasons, including its wild and interesting colonial background, its importance in the founding of the US, its gorgeous coastal scenery and incredible state parks, and its major urban centers like Boston. What truly sets it apart, though, is the state's welcoming and humble culture, where people find pride in their state while simultaneously learning and growing from its sometimes mottled past. Massachusetts has embraced diversity and now reflects that variety on so many of its wonderful Main Streets dotted with options for food, art, and entertainment. The state has become a welcoming, safe haven for permanent residents and visitors alike.