Aerial view of Fall colors in Chester VT.

7 Most Underrated Towns In Vermont To Take A Trip To

Vermont enlivens the imagination with many classic New England images, from firey autumn leaves to rolling farmland. The area became a state in 1791, fourteenth on the list of earliest US states, just after the Thirteen Original Colonies. Today, Vermont's mountains, lakes, and closeness to neighboring destinations like Massachusetts, New Hampshire, New York, and Canada all make the state a place that justifies its strong reputation. Some of the state's best features lie beyond its larger cities. These small towns, chosen for their modest size and outsized offerings for the visitor, deserve to be better known. 


Grafton Village Overlook, By Joseph W, CC BY 3.0, File:Grafton Village Overlook - panoramio.jpg - Wikimedia Commons
Grafton Village Overlook, By Joseph W, CC BY 3.0, File: Grafton Village Overlook - panoramio.jpg - Wikimedia Commons

Located in the heart of the Green Mountains, Grafton, population just 600, lies in the Green Mountains to the southeast of the state. Just west of the Connecticut River, which is the border with neighboring New Hampshire, the former wool-raising and textile mill town now welcomes tourists from around the world. The town runs a world-class cross-country skiing center, attracting athletes and amateurs alike. Pop into the Old Tavern, a downtown institution where many writers, poets, and artists have passed through. 

For foodies and especially cheese fanatics, Grafton offers some of the best artisanal cheese in the country, a tradition led by the Grafton Village Cheese Company. For a note of somber but important history, head to a local cemetery, which bears tombstones for many Grafton locals who died fighting in the Battle of Gettysburg, a key moment of the US Civil War. 


Aerial view of the cityscape of Montpelier, Vermont.
Aerial view of the cityscape of Montpelier, Vermont.

Montpelier is the capital of Vermont, but with 8,000 residents, it is the United States' smallest state capital. Settled in 1787, the town offers a long list of historic landmarks, including the Vermont State House and the Vermont History Museum, and the historic, nearly 200-acre Hubbard Park. For a more active experience, head to the bike trails around town, built by the Montpelier Area Mountain Bike Association.

For a sense of the past, even the town's name echoes with history: it shares the same title and spelling as the Virginia home of James Madison, a founding father and the fourth US president. The town draws inspiration from Montpellier, a city in the south of France, during a time when the French contributions to the American Revolutionary War sparked a fashion for all things French.  


Aerial view of fall colors in Chester, Vermont.
Aerial view of fall colors in Chester, Vermont. 

Chester, population 3,000, lies north of Grafton. The Williams River flows through this scenic place, making it an ideal weekend getaway. A tributary of the Connecticut River, the Williams allows for fishing, swimming, and natural beauty for town residents and visitors.

Chester is also known for its two historic districts, both of which are included on the National Register of Historic Places. The Stone Village shows granite houses from older times, and Chester Village exhibits beautiful buildings across two centuries of architectural styles, from Victorian and Colonial Revival to Federal. Chester makes a great spot for seasonal festivals: the town puts on its Fall Festival on the Green every September and its Winter Carnival each February. 


Equinox Pond and Mount Equinox at the Equinox Preservation Trust in Manchester, Vermont.
Equinox Pond and Mount Equinox at the Equinox Preservation Trust in Manchester, Vermont. 

Manchester sits in southwest Vermont and has about 4,500 residents. It has lived past lives as a sheep-raising town, a lumber center, and a hub for mining and stone quarries. The town boasts a major tourist attraction in Hildene, the estate of Abraham Lincoln's son Robert, which has a large and beautiful Georgian Revival mansion. The town also draws visitors to its American Museum of Fly Fishing, featuring rods, flies, and paraphernalia. The town is the headquarters of the fishing and clothing brand Orvis.  

The Southern Vermont Arts Center in town organizes a diversity of exhibits. Nature lovers will enjoy the path to Mount Equinox, which lies west of Manchester proper, or the Green Mountain National Forest, which is south of town. 

Bennington, population 15,300, has attracted thrill seekers and deep thinkers since its founding in 1749. The home of Bennington College as well as Southern Vermont College, this place, in the southwest corner of Vermont, is a celebrated New England-style college town. The town also hosts the final resting place of prominent American poet Robert Frost.

The town was the object of the Battle of Bennington, a Revolutionary War battle in 1777: though the fighting took place just west, in modern-day New York state, the American soldiers were defending an arms depot in Bennington town. Today, Bennington stands above the rest as the site of a large monument to the American Revolutionary War, in the form of a stone obelisk honoring the same battle. At 306 feet, it is the largest man-made structure in Vermont. 


Commercial stores and restaurants in the New England town of Brattleboro, Vermont. Editorial credit: jenlo8 /
Commercial stores and restaurants in the New England town of Brattleboro, Vermont. Editorial credit: jenlo8 /

Seated on the Connecticut RiverBrattleboro, population 12,100, promises plenty of interest for the traveler. The historic downtown captures the town's proud past and natural beauty. Lying just across from New Hampshire and near the border with Massachusetts, the town makes a great base for broader exploration in the central New England area. The town is so attractive that British author and world traveler Rudyard Kipling settled here after marrying a local woman in 1892. Kipling observed that town life gave Brattleboro's residents a "terrifying intimacy" in one another's lives. 

Popular sites in Brattleboro include the New England Center for Circus Arts, the Brattleboro Museum, and the Estey Organ Museum, which remembers the town's reputation as a manufacturing center of musical instruments. Outdoors enthusiasts should head for the Brattleboro Words Trail, as well as Fort Dummer State Park, where camping, biking, and hiking offer some of the state's finest natural settings.


Scenery of the Stowe Recreation Path, Stowe, Vermont.
Scenery of the Stowe Recreation Path, Stowe, Vermont.

Many Vermonters feel that Stowe, with 5,300 residents, is the state's best ski town. Home to the Stowe Mountain Resort, the town claims to be the "ski capital of the east." Sitting in the shadow of the picturesque Mount Mansfield, the town offers outdoor fun in warm-weather months, too. Mountain tourism has been a staple of the Stowe economy for a century. 

Among cultural interests, the town is home to the von Trapp family, proprietors of the Trapp Family Lodge, and who inspired the classic film The Sound of Music. The Stowe Village Historic District has been protected under the National Register of Historic Places since 1978. Stowe was, until his 2019 death, the home of Jake Burton Carpenter, founder of the Burton Snowboards company and a leader in making snowboarding the global phenomenon and Olympic sport that it is today.

Vermont's best towns are often underrated. 

Vermont has quite a bit to attract visitors, whether they come from down the road or half a world away. Small places like Grafton punch above their weight with athletic and nature opportunities galore. Chester has architectural wonders and cultural festivals that more than justify the drive. Stowe, meanwhile, offers great skiing and sports of the future. Bennington and Brattleboro balance war history with literary greatness, while Montpelier offers what may be the nicest and is certainly the smallest state capital you have ever seen. As these small, underrated towns suggest, Vermont's small size hides a large list of reasons to explore the state. 


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