10 Most Charming Town Squares In New England
New England is one of the most scenic regions in the US, notable for its four-season weather, vibrant art scenes, and quaint little towns that feel like home away from home. Each has unique characteristics, but they all have some of the most charming town squares in New England. These community hubs embrace the region's rustic, enchanting appeal while offering distinctive local finds and friendly communities.
From classic fishing ports in Maine to the fun and lively party atmosphere of Provincetown, these small areas have much to offer. Local communities gather in these entertainment and cultural hubs to host live events that showcase the best of New England spirit while adding their own charm. Check out the most charming town squares in New England.
Bar Harbor, Maine
Bar Harbor is a classic fishing village in Maine that also offers a fun and vibrant downtown area, one of the best in the region for shopping and dining. Downtown features buildings with traditional cedar shake siding painted in a variety of colors, adding a unique flair to the district. It is distinctive as both a beach getaway and a wilderness retreat, serving as the gateway to the Acadia Mountains and offering a charming aesthetic that complements its brightly painted structures.
The walkable roads lead to many shops and diners, like 2 Cats Restaurant & Inn on Cottage Street, renowned for its lobster rolls, a staple of the town's cuisine. Another landmark is the Criterion Theater, opened in 1932 and still a local favorite on weekends, making it one of the best local places to visit. Shore Path is worth a stroll on any visit, wrapping around the harbor and offering a peaceful respite from the bustle of downtown since 1891.
Kennebunkport, Maine
Historic Kennebunkport, Maine's downtown district, centers on Dock Square, a compact, walkable area along the Kennebunkport River. The classic New England appeal, colorful flowers, and inviting atmosphere make it one of the best districts in the region. An essential aspect of the area is its dining scene, with elevated options such as Boulangerie: A Proper Bakery during the day and 50 Local at night.
The local bakery specializes in artisan breads and pastries baked in a stone-deck oven, making mouthwatering goods that should not be passed over. 50 Local is a bistro that serves local ingredients and menu items, and is known as a neighborhood eatery. Both offer ideal opportunities to rub elbows with locals and walk away with a deeper appreciation for the town's culinary prowess.
Camden, Maine
Downtown Camden has a traditional feel, with walkable streets and brick storefronts that offer an inviting atmosphere. The small town offers plenty to see and do, with open spaces and unique architecture, including the 1928 Camden Public Library, which houses several fascinating collections that provide a glimpse into the town's heritage. The brick building and gazebo sit atop a rock wall resembling a castle buttress, giving the downtown area a distinctive tone.
The Camden Opera House is another landmark that brings the community together for many nightly events. This is a fun community, hosting fun events like Jazz in June, which also adds to the district's cultural side. This is one of the best town square districts to walk around in Maine, and the architecture and fun events make it hard not to book a second trip right away.
Provincetown, Massachusetts
P Town, as locals call Provincetown, has a fun, lively downtown area known for its festivals and party atmosphere. Commercial Street is the main strip, where visitors will discover unique finds, clubs, and charming eateries specializing in local ingredients. Provincetown Inn is at the end of Commercial Street and provides a unique glimpse into the town's natural side and harbor views.
Stroll in the other direction to discover the 1844 Eastern Schoolhouse for a peek into the past. Both exhibits show different sides of P Town, and these elements are what give it such character and charm. No trip to this area is complete without stopping at the Lobster Pot, where the owner is a local treasure and a great spokesman for the district. There is no shortage of things to do and see, and this exciting town square is one of the most fun in New England.
Portsmouth, New Hampshire
Downtown Portsmouth revolves around Market Square, where many go to catch an iconic view of the North Church Steeple, find a pub, or shop at one of the many retailers. This is the town's cultural hub and one of the best places to meet residents. Market Square and Market Street are also cultural epicenters, with museums and art galleries that add to their distinctive atmosphere, such as The Music Hall.
The Victorian-era theater is also home to a nightclub, making it a popular spot for locals and visitors alike. One of the best ways to see the district around Congress, Market, and Pleasant Streets is to take a guided walking tour. The tours depart twice a week from the Market Square Kiosk and showcase top sites and venues across the district to make the most of any visit.
Littleton, New Hampshire
Littleton's town square centers on historic Main Street and its Pollyanna statue, a tribute to hometown author Eleanor H. Porter. The open arms and welcoming smile sum up Littleton's welcoming spirit and friendly atmosphere. Littleton Diner is a downtown tradition, serving breakfast and town news to locals and visitors, and showcasing the area's quaintness. Several other landmark venues give the town its character, including the iconic Littleton Opera House.
The opera house is over 100 years old and is considered a Main Street staple, with its white siding and turret standing like a beacon in the night. Culture and the arts are a common theme throughout town, with the splendid White Mountains providing a natural backdrop for many artists, artisans, and others. While exploring Main Street, this work can be experienced at the League of NH Craftsmen and other galleries and events that make this town square area one of the most artistic in the state.
Mystic, Connecticut
The historic seaport of Mystic, Connecticut, has a charming downtown area with classic brick buildings along the famed Mystic River. The area has something for everyone, whether you're a history buff, a foodie, or looking for something to do, making this port a top tourist destination in the state. Pop Over Eatery specializes in American breakfast and lunch using local ingredients and is a top spot for fueling up for a day of discovery.
For a nightcap, there are several distinctive places to wind down, including the newer The Port of Call, a cocktail lounge serving small plates inspired by coastal delicacies. Downstairs from the lounge is the Dive, where patrons will find shuffleboard and vintage arcade games. Mystic is just a fun town, and this atmosphere, combined with hundreds of years of history, makes it one of the most charming districts in New England.
Montpelier, Vermont
Montpelier's town square is near the elegant Vermont State House, with its gold dome, and is surrounded by compact streets, shops, and pleasant eateries. The Winooski River flows through the area, adding to its appeal, which is further enhanced by traditional architecture and church steeples. A free walking tour of the state capital introduces visitors to the Roman goddess Ceres atop the dome and the statue of Revolutionary War hero Ethan Allen.
After visiting the capital, take a short hike up the wooded hill to Hubbard Park and climb the observation tower, circa 1930, for unobstructed views of the area. No visit is complete without sampling the famous maple syrup Vermont is known for. A short drive from downtown is Bragg Farm Sugarhouse and Gift Shop, specializing in a wide selection of products and gift items.
Brattleboro, Vermont
Brattleboro's Main Street is the heart of the downtown, often referred to as the town's square. Here, visitors will find storied architecture and brick buildings that offer a traditional aesthetic and unbeatable charm. The Round and Black Mountains add nuance to the area, as do the Connecticut and Western Rivers, each adding depth and natural beauty to the scene for artistic inspiration.
Local and regional art is easy to find downtown at galleries such as the Brattleboro Museum, which includes 15-20 exhibits in one of Southern Vermont's landmark museums. The Brattleboro Words Trail is another landmark where visitors can explore audio stories about the town's literary history, including tales about Rudyard Kipling. The Stone Church showcases the community's fun side, transforming a vintage church into a live music venue.
Woodstock, Vermont
Woodstock has New England charm, right down to the Middle Covered Bridge in its downtown district, brick structures, and cobblestone sidewalks. This serene setting is ideal for a shopping venture, and Woodstock's shopping district offers a toy emporium, boutiques, and landmark merchants. Landmarks include The Yankee Bookshop, established in 1935, which is selling vinyl records again after not doing so since the 1960s. Woodstock is one of the most classic New England towns in the region, and one of the best to visit.
Where New England’s Heartbeat Meets Its Hometowns
From classic seaports to quirky districts, these are the best town squares in New England. Each of these small cities has distinctive characteristics that set it apart, but they share a community spirit and friendly atmosphere that add to their natural beauty. Many historical elements, particularly maritime, contribute to each one's overall mystique.
P Town is famous for its party scene, but it is also a charming village to walk around. One cannot deny the maritime heritage that makes Mystic's seaport so fascinating, but there is also much more to the downtown area. One of the best reasons to hang around town squares is to mingle with the locals, and there may be no better districts for doing that than these 10 quintessentially New England downtown areas.
