2025's Most Underrated Towns In New England
With its centuries-old villages and rugged coastlines, New England is one of Northeastern America's most popular (and picturesque) tourist regions. It is also one of the oldest parts of the country, with many of its communities predating the American Revolution by decades.
From Massachusetts' beautiful Berkshire Hills to Rhode Island's scenic coastline, the best of the small towns in the six states comprising New England are captivating. Whether your interests lie in world-class museums or participating in cultural events and festivals, these underrated places to visit in New England in 2025 offer a unique taste of Americana that seems unchanged by the passing of time.
Stockbridge, Massachusetts
Stockbridge occupies a unique position in American cultural history, serving as both Norman Rockwell's final home and the inspiration for many of his best-known works. The town's Main Street, immortalized in Rockwell's 1967 painting, Stockbridge Main Street at Christmas, looks remarkably unchanged. Here you will find attractive old buildings like The Red Lion Inn, built in 1773 and enhancing one of the prettiest street scenes in the country (and yes, you can still book a room at this historic inn).
The Norman Rockwell Museum is a must-visit and houses the world's largest collection of the artist's original works, including over 570 paintings and drawings. In addition to permanent displays of artwork by Rockwell and other American artists, the museum features temporary exhibits, too. For 2025, these include I SPY: The Hidden Wonders of Walter Wick alongside accompanying outdoor sculptures. Rockwell's original studio, moved to the museum's 36-acre campus, is open to visitors from May through October and remains unchanged, with his art materials, library, and personal items still on view.
Other cultural highlights include the Berkshire Theatre Group’s regular roster of professional productions. These are staged at its two venues, the historic Colonial Theatre and the Unicorn Theatre. Tanglewood, summer home of the Boston Symphony Orchestra, is just a few miles away in neighboring Lenox and offers tours as well as dining and accommodations.
Chester, Connecticut
Its location in the Connecticut River Valley certainly hasn’t hurt Chester’s prospects when it comes to attracting tourists. The town's picturesque Main Street curves along Pattaconk Brook, its attractive 19th-century buildings now home to art shops like the Chester Gallery and the Lori Warner Studio/Gallery with their local and regional art displays. Summer weekends in 2025 are a great time to visit as the Chester Sunday Market will be bustling with shoppers and vendors along Main Street, accompanied by live music.
The town’s most unique attraction is the Chester-Hadlyme Ferry. This designated Connecticut landmark has been running since 1879, providing a fun eight-minute journey across the Connecticut River complete with superb views of the famous Gillette Castle. It is also very practical as it will save time if you aim to explore both sides of the river.
Nearby attractions include Cockaponset State Forest, Connecticut's second-largest state forest. It is also popular among fishermen for its well-stocked Pattaconk Lake. Cedar Lake is just a few minutes’ drive and features safe designated swimming areas, picnic facilities, and boat rentals. For a unique and often overlooked family experience, visit Chakana Sky Alpacas for a tour and a chance to interact with these adorable creatures.
Grafton, Vermont
Few places in Vermont are as picturesque as Grafton. This idyllic small town has everything you would expect from a classic dose of Americana, from attractive white clapboard buildings, classic covered bridges, and even a town common that hasn’t changed since the town was founded in 1754. Every inch is like a living history museum; highlights include visiting Grafton Village Cheese. Founded in 1892, this dairy cooperative still churns out (pardon the pun!) award-winning cheddars using milk from local farms. Be sure to also visit their retail store for free tastings of their naturally aged cheeses, including varieties aged up to four years in underground caves.
The Nature Museum in Grafton is another must-visit. Highlights include exhibits on local flora, fauna, and geology, as well as grounds that feature native plant gardens, a frog pond, and access to the Village Park trail system. Their annual Fairy House Festival, held in September, is a great excuse to visit Grafton as the Nature Museum transforms into a whimsical wonderland.
Like history? Then visit the Grafton Historical Society Museum for its displays of artifacts representing over 250 years of local history. The Turner Hill Interpretive Center is also interesting and tells the remarkable story of escaped slave Alec Turner and his family, including his daughter Daisy Turner, who became a renowned Vermont storyteller. Grafton is also an integral part of Vermont's African American Heritage Trail, which connects to other related historic sites.
Castine, Maine
Its location at the mouth of the Bagaduce River in Maine led to Castine being a much-contested strategic prize since the early 1600s. The town’s early colonial history is fascinating as at various times it found itself under French, Dutch, British, and American flags, each leaving behind fortifications and historic sites across the peninsula. You will learn more about this fascinating era with a visit to the Maine Maritime Academy, an institution that dominates the waterfront. Be sure to also check out its 500 ft long training ship, the State of Maine, which serves as both a working vessel and tourist attraction (tours are available when it is in port). The academy's 35-acre grounds are fun for a wander and overlook Penobscot Bay.
The Castine Historic District is also fun to explore. Encompassing the entire southern tip of the peninsula and much of the town, here you will find exceptional examples of Georgian, Federal, and Greek Revival architecture dating from before 1860. A self-guided walking tour can be picked up from the Castine Visitor's Center on Main Street. Must-sees include Fort George at the north end of the main drag, built by the British during the War of 1812 and boasting superb views of Penobscot Bay from its earthwork fortifications.
Further along the peninsula, the Wilson Museum explores the area’s natural history as well as the cultural heritage of the Penobscot Bay region through its collections and exhibits. Historic buildings on the grounds include John Perkins House and a working blacksmith shop. The Castine Historical Society, located in the restored Abbott School building, is also on the route and presents rotating exhibits on local maritime and military history.
Peterborough, New Hampshire
The old colonial town of Peterborough holds a special place in American cultural history. Home to MacDowell, the nation's oldest artist residency (it was founded in 1907 by composer Edward MacDowell), this 450-acre property has hosted more than 9,000 artists down the years, members of which have won Pulitzer Prizes and National Book Awards. Notable orks created here include Thornton Wilder's Our Town, a much-respected artwork that was modeled on Peterborough itself.
A great time to visit Peterborough is during its popular First Friday events. Held downtown on (you guessed it!) the first Friday of each month, these family-friendly happenings include free art presentations and talks, live performances, shopping, and food and drink experiences. And 2025’s Medal Day celebration on June 29 is another great excuse for a visit; it’s when visual artist Alfredo Jaar is being presented with the 65th Edward MacDowell Medal in a public ceremony.
Other downtown cultural highlights include the Mariposa Museum, which celebrates folk art from around the world with hands-on exhibits; and the Monadnock Center for History & Culture, housed in a restored 1840s building and presenting rotating exhibits on regional history as well as a rich program of cultural events year-round.
Whether you are a day tripper, a weekend warrior, or are looking for somewhere solid for a great 2025 vacation, these truly authentic New England towns are just the ticket. Often overlooked by tourists visiting the usual destinations, each has managed to hang on to its distinct personality despite centuries having passed. Together, these underrated towns in New England offer genuine connections to the region's rich history and culture.
