8 Prettiest Main Streetscapes In Massachusetts
Broad boulevards and bustling thoroughfares lined with inviting restaurants, street-side patios, independent shops, and traces of history are a quintessential element of many small communities, and Massachusetts is no exception. From coastal Cape Cod treasures like Chatham and Provincetown, where local culture has been influenced by generations of industry and creativity, to spots like Concord, which carry the mark of some of the most significant moments in American history, these downtowns run the gamut. But which are truly magical? Continue reading to discover the prettiest streetscapes in Massachusetts.
Newburyport
One of Massachusetts' most appealing coastal destinations, Newburyport is on the Merrimac River, just 35 miles from Boston. Looking out across the water, you can practically picture the old ships arriving, laden with molasses destined to become rum. Today, many things have changed, yet Newburyport's history lingers in the Federalist architecture, the cobblestone streets, and the salty air of its beloved Market Square. Custom House Maritime Museum, on busy Water Street, is a nostalgic space boasting three floors of exhibit rooms packed with information, memorabilia, and art from the colonial era, the Revolutionary War, and Native peoples who lived on the land long before the arrival of European settlers.
East meets west at neighboring Poynt Newburyport, a stylish restaurant brought to Newburyport from La Jolla, California, with outdoor seating to maximize its location along the water. Illume Books is warm and beautifully curated, with an equally diverse selection of games and art to make visitors feel at home. Whether you’re looking for your next great read, the perfect gift, or simply a cozy place to spend some time, this bookstore will exceed your expectations. Meanwhile, Waterfront Promenade Park, just off Water Street, is an outdoor space with swings and hammocks, as well as a well-maintained boardwalk that's nice for an evening stroll.
Concord
If you have yet to visit Concord, it's time you explored one of Massachusetts’ most picturesque and historic areas. As the site of the first battle of the Revolutionary War in 1775 and the "shot heard round the world," the atmosphere today is thankfully quiet and peaceful, with beautifully preserved homes dotting the streets downtown. Old North Bridge, where the American Revolution began, is an evocative place to walk, given its role in shaping the history of the United States.
Concord’s Monument Square and Main Street showcase classic New England town charm with historic shops, colonial architecture, and local eateries, including Caffè Nero, situated right across the street from the Concord Visitor Center. It’s a Euro-style coffee shop in a large, vintage-inspired space, offering something on the menu for just about everyone. The Concord Free Public Library is a historic institution with impressive architecture, complemented by a vast selection of resources, such as nearly complete runs of all newspapers published in Concord since 1816. To get a better feel for the town's history and heritage, the Concord Museum is certainly the go-to place. Exhibit highlights include Paul Revere's lantern and a bust of Ralph Waldo Emerson, as well as a writing desk, snowshoes, and several other items that once belonged to Henry David Thoreau.
Provincetown
Provincetown is another picture-perfect seaside town on Cape Cod. Commercial Street boasts a vibrant, eclectic energy, featuring galleries, seafood restaurants, unique shops, and stunning harbor views. PTown, as it's known to locals, is the oldest continuous artist colony in the United States, and the Provincetown Art Association and Museum (PAAM), which has 5 stunning galleries, has been promoting and supporting the work of local artists for over a century. Fuel up before or after you visit with a taste of local flavor at the Provincetown Portuguese Bakery, a downtown fixture for generations.
Further along is Whalers Wharf, a shopper's paradise with multiple floors and dozens of local shops, studios, restaurants, and galleries. At the end of the wharf is the beach and Ptown Harbor, where you can go for a stroll and dip your toes in the bay. In the evening, catch a live performance at the Provincetown Theater, a cultural gem renowned for its intimate atmosphere and diverse repertoire.
Marblehead
A sleepy town built on a rocky peninsula and beloved for its well-preserved 18th-century buildings, Marblehead is another Massachusetts jewel with an incredibly photo-worthy Main Street. The town has a rich naval history dating all the way back to its pivotal role in the American Revolution. Today, the town strikes as a beautiful time capsule, with streets looking much the same way they did back then. Washington Street runs through Old Town and has long been the town’s primary commercial and social artery.
Abbot Hall, built in 1876 and listed on the National Register of Historic Places, showcases extraordinary exhibits of Marblehead's proud patriotic history, including the iconic painting Spirit of '76, originally titled Yankee Doodle, by Archibald Willard. Elia Taverna Marblehead, located further down Washington Street, is an authentic Greek restaurant serving delicious dishes, including lobster risotto, moussaka, and keftedes. As you continue to explore the Historic District, you will come to Old Burial Hill Cemetery, one of the town's landmark attractions and one of the oldest graveyards in New England.
Northampton
Northampton is home to one of New England's most beautiful university campuses. The 150-year-old Smith College, located at the edge of downtown, boasts such notable alumni as Gloria Steinem and Sylvia Plath, and is one of the largest women's colleges in the country . Northampton's compact downtown, just a mile from the Connecticut River, brims with historic buildings, including well-known landmarks such as the Academy of Music, which was the first municipally-owned theater in the country in 1892. Today, it presents a wide range of films and live shows in a beautifully preserved theatre.
Main Street is a vibrant and pedestrian-friendly area, lined with independent bookstores, cafes, and other local businesses. Between the Academy and City Hall is Pulaski Park, a delightful spot featuring a grassy area and benches where you can sit and take a break. If you are craving a bite, T. ROOTS is a Taiwanese restaurant serving street food and vegetarian dishes, including tofu salads and scallion pancakes.
Nantucket
It's perfectly normal in Nantucket to see flip flops padding down cobblestone streets, weaving between steepled churches framed by majestic elms and pastel-colored buildings with weathered shingles. Main Street spans ten blocks between Quaker Road (Caton Circle) and Straight Wharf, and is packed with restaurants, shops, and boutiques like It's a Shore Thing, a gift shop offering nautical-themed souvenirs.
Mitchell's Book Corner boasts an impressive variety of interesting titles and features a section dedicated to Nantucket's rich whaling history, making this small-town gem a bibliophile's paradise. Steps away on Water Street is the Dreamland Film and Performing Arts Theatre, housed in an old building that has retained much of its original character. Be sure not to miss the Nantucket Whaling Museum on Broad Street, which tells the story of Nantucket through a variety of interactive exhibits and engaging presentations.
Stockbridge
In the heart of the Berkshires, Stockbridge boasts one of the most festive Main Streets in America. It is like being in a Hallmark movie, and it is not just because Norman Rockwell, the celebrated American painter best known for his warm, detailed depictions of everyday life in the United States, lived and worked right here. Still, the fact that Rockwell was inspired by Stockbridge’s classic small-town beauty speaks volumes. You will find beautiful old houses such as the Historic New England Merwin House, a late Federal-style masterpiece overlooking the Housatonic River, which now serves as a museum.
The iconic Red Lion Inn also sits casually along Main Street, despite being one of America’s last great 18th-century hotels with a history of accommodating people like Calvin Coolidge, Franklin D. Roosevelt, Nathaniel Hawthorne, and Henry Wadsworth Longfellow. And across the street, St. Paul’s Episcopal Church is a Norman-style building designed by Charles F. McKim in 1884. McKim later joined William Rutherford Mead and Stanford White to form McKim, Mead & White, which became one of the most successful and influential American architectural firms of its time in the United States.
Chatham
With a settlement history dating back to the 1660s and an economy once centered on fishing, shipbuilding, and salt production, Chatham has many beautiful stories to tell. Chatham’s Main Street is highly walkable and features dreamy waterfront views, especially as you stroll toward Chatham Lighthouse, set in the "elbow" of Cape Cod.
There are some hidden gems in the downtown area, including Yellow Umbrella Books, which keeps a great selection of new and used titles, with sections specific to local authors and Cape Cod history. Chatham Orpheum Theater, which dates back to 1915, presents new releases and the occasional live performance in a historic venue. If you follow Main Street to the end, you'll arrive at Lighthouse Beach, a beautiful place to lock eyes with seals resting on the sandbar.
Main Streets don’t have to be rendered in neon and technicolor to be worthy of a visit. Storied legacies, beloved landmarks, and natural beauty make these downtowns come alive. In Massachusetts, the most picture-perfect streetscapes are salt-streaked, time-worn, and utterly unforgettable, despite being far removed from urban centers and tourist hotspots. These towns are waiting to be discovered, but the good news is that the longer they wait, the more beautiful they become.
