9 Towns In New England With Vibrant Downtown Areas
While New England’s famous cities often take center stage when it comes to their downtowns, there is much to be said about the region’s humbler Main Streets. Cities like Boston and Providence certainly boast larger attractions, wilder nightlife, and more visitors, but for those craving all of this on a more intimate scale, New England’s small towns are the way to go.
In addition to lacking shoulder-to-shoulder city crowds, these 9 New England towns and their vibrant centers promise spirited art scenes, charming historic districts, and intriguing local businesses you will not find anywhere else. Along with dazzling local festivals and events, these small towns may just surprise you with how much their downtowns have to offer. So, if you are looking to swap your Starbucks for a cozy local cafe, add these nine vibrant downtowns to your travel itinerary in 2024.
Mystic, Connecticut
While the village of Mystic once rose to fame as a shipbuilding center in the 17th Century, today, the river town is known for attractions like the Mystic Aquarium (the only place in New England with Beluga Whales). But fun on land is just the beginning of what this maritime village has to offer. With Mystic’s namesake river flowing right through the historic downtown, visitors can paddle the gorgeous waters with rentals from Adventure Mystic or take a more laid-back excursion with Mystic River Cruises.
Back on land, downtown Mystic boasts stunning waterfront views and over 80 independently-owned shops and art exhibits to explore, like the Hang the Moon gift shop and Trade Winds fine arts Gallery. New England seafood is also a Mystic specialty, with upscale restaurants like Oyster Club and more casual digs like The Mariner, a nautical-themed seafood joint. As a follow-up, the Downtown River Shuttle Service will bring visitors straight to the Mystic Seaport, famously known as the largest maritime museum in the United States.
Littleton, New Hampshire
At the northern edge of New Hampshire's White Mountains, Littleton is another delightful New England town with a gorgeous river running through its center. The mighty Ammonoosuc serves as the centerpiece of Littleton's Main Street, inviting visitors to explore the river’s beauty along with countless specialty shops and landmarks lining its downtown Riverwalk.
Complete with a covered pedestrian bridge and breathtaking views, the Riverwalk grants passage to historical landmarks like the Renaissance Mills of Littleton and riverside pubs like Schilling Beer Co. Downtown Littleton also boasts historic sites like the 19th Century Opera House and whimsical attractions like Chutters candy shop, home of the world's longest candy counter. For art enthusiasts, Main Street is also the location of the town’s 55th Annual Littleton Art Show, set to take place September 28th, 2024.
Portsmouth, New Hampshire
Portsmouth, New Hampshire’s original state capital, is another river town with beauty to spare. While not flowing directly through Portsmouth’s downtown, the Piscataqua River is just a short walk away at green spaces like the 10-acre Prescott Park. The park’s enchanting waterfront gardens are a lovely follow-up or introduction to Portsmouth’s downtown, particularly the nearby “Market Square.”
With buildings dating back as far as the 17th Century, Downtown Portsmouth is heaven-on-earth for history buffs. The 90-minute Historic Portsmouth Walking Tour is the best way to see more of the architecture and historic sites, departing right from downtown to follow the Portsmouth Harbour Trail. Later, once the sun sets, Market Square’s nightlife brightens the downtown with attractions like Jimmy's Jazz & Blues Club, The Music Hall Lounge, and the Port City Pub.
Montpelier, Vermont
Nestled in the heart of north-central Vermont, Montpelier, the charming state capital, offers a classic small-town experience. Unlike other state capitals, this Hallmark town is free of big-box chains, allowing locally owned businesses to shine and maintain a quaint and cozy downtown. Visitors can explore an array of independent shops, such as the beloved Bear Pond Books and the Artisans Hand Craft Gallery, housed in pristine historic buildings.
With a nostalgic preservation of small-town America, it is unsurprising that USA Today once rated Montpelier the “#1 Best Small Town for Shopping in the United States.” Adding to the allure just steps from independent antique shops like J. Langdon and cute cafes like Capitol Grounds, the Winooski River is a delightful interlude. As for those looking to experience the town’s art and culture, downtown Montpelier will come to life with its spirited ArtWalk events on the first Friday of October and December of 2024.
Brattleboro, Vermont
Named 1 of the “10 best small towns in America” by Fodor's Travel, Brattleboro is another artsy Vermont town known for its laid-back town center. Its downtown shares many similarities with Montpelier, including the historic brick buildings and river views. In this case, the racing Connecticut River runs right through the heart of Brattleboro, straddling the downtown area.
Mirroring Montpelier even further, the shopping in downtown Brattleboro is fantastic, and nearly all shops and restaurants are locally-owned. Highlights include Brattleboro Books, Twice Upon A Time Antiques, and Amy's Bakery Arts Cafe to name a few. As for other ways to embrace the town’s artistic side, the Vermont Jazz Center and Brattleboro Museum & Art Center are the perfect follow-up. Additionally, on the first Friday of every month from May through October, Downtown Brattleboro’s Gallery Walk celebrates local artists in an exciting way, supplying food trucks, live music, and interactive art stations.
Greenfield, Massachusetts
Described as having a “Good, Old-Fashioned Downtown,” Greenfield is the embodiment of simpler times. Like Montpelier, this charming Massachusetts town values a sense of community and spotlighting mom-and-pop businesses like Alchemy of Avalon, Antique Revival and Collectibles, and Greenfield Records. Even the town’s historic movie theater is independently owned, making the Greenfield Garden Cinemas a perfect place to see a show while supporting a local business.
Beyond its pleasant shops and businesses, the downtown Greenfield Farmers Market is a delightful start to any Saturday, with live music, local produce, and independent vendors. Other events, like the annual Greenfield Vintage Days festival, celebrate the town’s old-fashioned spirit. This year's festival (happening October 11th to 13th, 2024) will feature vintage car shows, old-school trolley rides, and other retro festivities in downtown Greenfield.
Pittsfield, Massachusetts
For a downtown with more of a city atmosphere, Pittsfield is a great (albeit underrated) alternative. With just under 43,000 residents, this Berkshire County community features the perfect balance between laid-back and bustling, promising art and culture without the big-city crowds. Downtown Pittsfield, also called the “Upstreet Cultural District,” lives up to its name with attractions like the renowned Berkshire Museum and Boyd-Quinson Theater.
Along with a wealth of art and culture, Pittsfield is thought of as a “City of Festivals.” And while some of the town's premier events have already taken place, there are still plenty of exciting events on the horizon in Downtown Pittsfield in 2024. Highlights include the Saturday Pittsfield Farmers Markets, the September Summer Music Series, and the highly anticipated "It's Alive!" Halloween event scheduled for October 19th.
North Adams, Massachusetts
For the introverted art lovers, North Adams is an even quainter Massachusetts town with a vibrant art scene. This town of 12,000 locals may be small, but it is also home to the largest contemporary art museum in the United States. Located in a former printing factory, the Mass MoCA stands as the town's symbolic centerpiece. As for North Adams’ downtown, the Massachusetts College of Liberal Arts infuses the area with a free-spirited, artistic energy.
Nearby, visitors can explore the Berkshire Art Museum, Gallery North, and charming tea rooms like Heart's Pace. Centered around the college, the area’s businesses foster a lively academic atmosphere that welcomes students and non-students alike. Both groups are also encouraged to join North Adams’ riveting downtown events throughout the year, like the Northern Berkshire Fall Foliage Parade on October 6th, 2024, and next year’s WinterFest, happening the third weekend in February.
Wakefield, Rhode Island
Finally, for “The Perfect Day Trip Destination,” Wakefield has a downtown whose charms enchant all who pass through. Settled in the 18th Century for its closeness to the Saugatuck River, the beauty of this Rhode Island river town still attracts people to this day. Carefully maintained by the Wakefield Village Association, Downtown Wakefield is known for its walkability and river views, so make sure to wear some comfy shoes when you explore the town’s charms.
Historic Main Street is where the majority of the magic happens, with tons of cozy, locally-owned restaurants like Meldgie’s Rivers Edge and Tavern on Main. Dotted in between, you will find cute old-school businesses like Main Street Candy and more quirky landmarks like Purple Cow Co, whose bright purple storefront is impossible to miss. All in all, this adorable New England town may not have the flashy big-city attractions, but for many, this is a breath of fresh air.
Final Thoughts
While New England’s big-city downtowns offer plenty of attractions, the charms of the region's smaller communities are equally worth exploring. From Greenfield’s “Good, Old-Fashioned Downtown” to the lively, artsy vibe of Pittsfield’s town center, there is an atmosphere for any type of traveler. With that being said, there is one thing that connects them all: the friendly New England locals excited to show you the vibrant spirit of their Main Streets.
