9 New England Small Towns With Unmatched Friendliness
New England, located in the northeastern United States, boasts topographical diversity, ranging from coastlines to mountain ranges. Its history spans hundreds of years, and this history is reflected throughout the many cities that make up its landscape. The small towns are known for their vibrant, friendly atmosphere and community events that celebrate the remarkable culture and heritage that make this region so memorable.
These hamlets are fun to visit at any time of the year, with each season offering something new. However, the affable residents who make up the towns remain the same. Hanging out at local diners or attending regional community events is often the best way to experience what each place offers. Here are nine New England towns with unmatched friendliness that are worth seeing.
Woodstock, Vermont
Woodstock is a sparsely populated community that is big on fun. Life revolves around the town square, known simply as the Green, which is home to many community events. Market on the Green is a weekly farmers market from June through October that showcases the friendliness of the residents and is an excellent time to visit. Another community festival is the popular Woodstock Art Festival. The weekend-long event features over 30 New England artists, live music, and food on the weekend following Labor Day.
Other festivals celebrating the region include the Apple & Crafts Fair, the Sculpture Fest, and the Woodstock Digital Media Festival. Don't miss a chance to walk around the Village. The pleasant stroll will lead you past the stunning architecture and around the Ottauquechee River, and may be one of the most picturesque walks you've ever taken.
Brattleboro, Vermont
Brattleboro is a charming city with classic brick storefronts and an affable atmosphere. Hippie communes were prevalent in the 1960s and 1970s, contributing to the town; it is not a stretch to say that Brattleboro is an intentional community. Many come to see several cultural venues, such as the New England Center for Circus Arts and the Vermont Jazz Center.
Live events and festivals bring crowds together to celebrate this slice of New England. The Gallery Walk, from May to December, honors Brattleboro's artistic side, from The Market to The Stage, featuring local artists and live music. Bratt LUV Crawl is a quirky pop-up Valentine's Day pub crawl featuring whiskey, maple syrup, and chocolate, showcasing the entertaining side of the neighborhood.
Warren, Rhode Island
Warren is one of the smallest towns in the smallest county in the smallest state in the United States, and proud of it. The charming beach neighborhood must have strong community ties to thrive, and this lends a friendliness that is hard to match. The sleepy district has an affinity for the outdoors and features the East Bay Bike Path, a standalone bike path that runs through the middle of town, with plans to expand.
Jamiel's Park is the community hub where many gather for family events and festivals, such as Bristol/Warren Art Night, which offers free educational programs. The residents also created Hope and Main, a local food campaign that serves as an incubator for regional restaurants. Another friendly event in town that people love is Burr's Hill Park Band Shell, a summer concert series.
Bar Harbor, Maine
Bar Harbor is a fantastic walkable town with classic New England architecture in the shopping district and a charming, salt-tinged atmosphere. It is the gateway to Acadia National Park, offering views of Cadillac Mountain, and provides substantial birding and outdoor opportunities. The friendly community gathers frequently to celebrate natural beauty through live events like the Acadia Birding Festival and Puffins and More.
Residents enjoy social gatherings, as evidenced by the town's calendar of events. Cultural venues include the Dawnland Festival of Arts and Ideas and the Bar Harbor Town Band Concert. If you visit during the summer, be sure to catch an outdoor movie at Seaside Cinema on Wednesday nights at Agamont Park, where you can enjoy it with the neighbors.
Brunswick, Maine
Brunswick is a designated Main Street community known for its quaint atmosphere and charming venues. The quintessential college town is renowned for its shopping areas like Maine Street and the Town Mall, which feature vibrant stores. Among the many cultural sites is the home of literary legend Harriet Beecher Stowe, now a National Historic Landmark.
In town, the locals hang out at Brunswick Diner or Dutchmen's Wood Fired Bagels to catch up on local news. Fun festivals are held in Brunswick throughout the year, highlighting the fun side of this coastal village. Claws N' Country Music Festival and the Brunswick Outdoor Arts Festival are two options in the summer.
Meredith, New Hampshire
Scenic Meredith is a quintessential New England town known for its natural beauty and small-town charm. It is the type of place where you want to spend as much time as possible outside, and the residents generally do. Start the day by exploring downtown's Sculpture Walk that winds through the picturesque streets. The sculptures complement the natural scenery and are a highlight of this area.
After spending the morning exploring the unique public art, lunch at Hermit Woods Winery and Deli, known for its artisanal wines made from blueberries and other local fruit. For the best experience, tourists should plan their trip in July to attend the annual New Hampshire Music Festival. The event has been held for over 70 years, drawing world-class musicians and thousands of fans.
Portsmouth, New Hampshire
Historic Portsmouth is one of the prettiest towns in New England. The landscape is filled with 17th and 18th-century mansions, many of which are found at the Strawbery Banke Museum. Some notable landmarks in the museum are the Lowd House and Bailey House, both dating back to the 18th century. The warm and inviting residents add a friendly depth to match the stunning scenery, especially at weekly gatherings like theatre productions at The Music Hall, an 895-seat venue.
Walking through the magical downtown is a must for any visit. Here, you will find quaint cafes, such as the Black Trumpet Bistro, and beautiful gardens like Prescott Park. This is a walkable city, and there are always people milling about. The downtown section has an old-world feel, underscoring the city's rich history, and the friendly merchants will have you coming back for another visit.
Mystic, Connecticut
Mystic is a historic village on the banks of the Mystic River, known for its rich maritime heritage and timeless New England charm. This riverfront town is filled with interesting corners to explore, but starting downtown is always a good idea. Here, visitors can admire historic captains’ homes, church steeples, and the iconic Mystic Drawbridge that still operates daily.
In summer, Mystic comes alive with events that bring the community together. One favorite is the Mystic River Jam, held every July at the historic Mystic Shipyard, featuring local bands and food vendors. Another quirky highlight is JAWSFest, which celebrates the classic movie filmed nearby. Visitors can also explore the area’s many vineyards and meet local vintners at Saltwater Farm Vineyard or Jonathan Edwards Winery, both offering tastings in scenic settings.
Provincetown, Massachusetts
"Ptown," as the locals refer to Provincetown, is a fun and vibrant city that knows how to have a good time on the northern tip of Cape Cod. The laid-back residents boast an eclectic art scene that can be explored at galleries such as The Provincetown Art Association and Museum (PAAM). Other notable galleries include the Provincetown Fine Arts Works Center and Ptown's East End, also known as the Gallery District.
The community celebrates its eccentricity at various events, including Great Music on Sundays, which takes place from June to December. Other events include the Provincetown Portuguese Festival and the Provincetown Jazz Festival. This is an outstanding place to visit at any time of year.
Finishing Thoughts
New England is a stunning region with beautiful coastal towns, unique architecture, and some of the oldest histories in the United States. The landscape is also known for its friendly communities that call the region home. Visiting these destinations during one of the many festivals highlights the sense of community among the residents and makes you feel at home. Downtown spots are generally the best places to mingle with locals, and these nine towns do not disappoint. As visitors stroll around centuries of maritime history, they are greeted by friendly merchants and unique finds. Bar Harbor is a prime example of this unique phenomenon, characterized by its compact streets and colorful buildings. If you are looking for a quaint getaway with unmatched friendliness, these nine towns in New England are unbeatable.
