9 Cutest Small Towns In Vermont For 2025
Vermont brings to mind classic New England scenes, whether of bright autumn leaves, cute college towns, or snowy hills and mountains. Bordering three other US states and Canada, the "Green Mountain State" was the 14th state to join the Union in 1791, just after the group of early US jurisdictions comprising the 13 original colonies. Today, Vermont's Green Mountain region, scenic rivers and lakes, and verdant forests make this place a favorite destination for many visitors. Vermont's tourist motto, "Vermont, Naturally," suggests why the state is an obvious choice for a getaway in 2025.
Brattleboro
Set along the Connecticut River in southeast Vermont, the town of Brattleboro holds out lots of ideas for the first-time or repeat visitor. Cultural hotspots include the Brattleboro Museum & Art Center, which is focused on local history, and the Estey Organ Museum, which honors the town's legacy as a manufacturing hub for musical instruments.
Literary lovers enjoy the Brattleboro Words Trail, a community-created, GPS-triggered audio tour of the town's literary and historical legacy. Outdoor enthusiasts flock to Fort Dummer State Park, which has biking, camping, and hiking among some of Vermont's loveliest nature. And since it sits near New Hampshire and Massachusetts, Brattleboro serves as a great jumping-off point for exploring the region.
Dorset
In Vermont's southwest corner, near the New York state line, the town of Dorset looks like postcard New England. Its menu of natural areas runs long, and topping the list are Dorset Peak, Bromley Mountain, Emerald Lake State Park, and the Dorset Hollow hiking zone.
The town also has much in the way of history. Dorset hosted a number of key gatherings that charted Vermont's course toward statehood. A former quarry site, Dorset provided marble for the New York Public Library, among other notable buildings. Dorset can be proud of its contributions to society, too.
Elmore
With fewer than 900 inhabitants, tiny Elmore, in the state's north-central zone, stands as a beloved, quiet destination for autumn leaf-peepers. For a look at real-deal classic New England architecture, check out Fisher Bridge, a covered bridge in the regional style, just east of town. Among Elmore's small-town quirks, the town seems to enjoy naming its points of interest after itself: Elmore town is separate from East Elmore. Elmore Mountain stands to the town's west. Elmore State Park lies north of Elmore town, and Elmore Lake provides waterside respite on hot days. In fact, it is often cited as one Vermont's prettiest lakes. Elmore Lake drains via Elmore Pond Brook into the Lamoille River.
Visitors needing a city break, or a break from all the Elmores, can opt for trendy Burlington, an hour's drive west.
Manchester
Manchester, in southwest Vermont, has even more history than most New England places. The town is home to Hildene, the manor estate of Abraham Lincoln's son, Robert. The property features a Georgian Revival mansion and attracts visitors from far and wide. Manchester also has the American Museum of Fly Fishing, with vintage rods, reels, and equipment of all types. After all, this is the headquarters of Orvis — the iconic American fishing and clothing brand, and the oldest mail-order retail brand in the United States.
Nature enthusiasts will want to see Mount Equinox, which is west of town, and the Green Mountain National Forest, which is to the south of Manchester. The Southern Vermont Arts Center here puts on diverse exhibitions and maintains a sculpture garden, a performing arts venue, and local forest paths and walking trails.
Middlebury
Middlebury has earned a reputation as one of the quintessential college towns in Vermont, if not the broader New England region. Founded in 1761, this is home to Middlebury College. The town lies east of Lake Champlain, a long, picturesque body of water dividing Vermont from New York State.
Middlebury College's lovely campus, which has stone buildings and the popular Middlebury College Museum of Art, is a favorite for creative sophistication and travelers seeking a genteel experience. Since the school's founding in the year 1800, the campus has edified students, professors, intellectuals, and visitors. In addition to Middlebury's campus, other walking options include Mean Woods, Battell Woods, Otter View Park, and Chipman Hill Park — all in close proximity to downtown Middlebury.
Montpelier
Montpelier may be the capital of Vermont, but with just 8,000 inhabitants, it is the absolute smallest of all U.S. state capital cities. (The second-smallest, which is Pierre, South Dakota, has 14,000 people.) Established in 1787, Montpelier was named the state capital in 1805. It offers numerous historic landmarks, including the Vermont State House and the Vermont History Museum, not to mention the 200-acre Hubbard Park.
The Winooski River flows through the heart of Montpelier, bringing nature to the town's urban center. Buddy's Famous, a popular hamburger place downtown, caters to all-American appetites.
Rutland
The central Vermont town of Rutland combines history and culture. Visitors often stop first at the Rutland County Museum, or at the Wonderfeet Kids' Museum, which aims to fuel children's imaginations via the "power of play," according to their website. Culture aficionados love the Rutland Historical Society, whose grounds hold a small museum dedicated to local themes.
More active types like Pine Hill Park, which has green woods and mountain biking trails. In fair weather, golf fans should head for the Rutland Country Club. Come winter, skiing or snowboarding at Killington, the glamorous resort just east of town, is a must-do experience for snow sports fans.
Stowe
In north-central Vermont, the town of Stowe competes with Rutland for the title of Vermont's best downhill skiing. Home to the Stowe Mountain Resort, Stowe claims to be the "ski capital of the east." And since 2002, it has hosted the Vermont Ski and Snowboard Museum. Bringing together sports, industry, and culture, Stowe was the home of Jake Burton Carpenter, the founder of the Burton Snowboards company, until his death in 2019. Carpenter's vision for snowboarding made the sport a global phenomenon and an Olympic event.
Stowe is also associated with the von Trapp family, owners of the Trapp Family Lodge, which inspired the 1965 movie classic, The Sound of Music. The lodge remains in operation today.
Woodstock
Woodstock, not related to the town and 1969 cultural moment in New York state, is a favorite among architecture fans. This southeastern Vermont town offers gems like the First Congregational Church, built in 1807, which boasts a bell cast by famous American revolutionary Paul Revere. Woodstock also has the Norman Williams Public Library, completed in 1884. Woodstock has more recently enhanced its infrastructure through digital technology: since 2011, the "Wireless Woodstock" program has established free wireless internet for the whole town.
For time outdoors, the Woodstock Town Forest offers walking and natural bliss, just north of town. The Marsh-Billings-Rockefeller National Historical Park provides majestic views over the region. Fun fact: the park is the only part of the US National Park system in Vermont, except for the Appalachian Trail.
Vermont's Small Towns Are Among Its Cutest
With so much variety in this small state, it is little wonder that Vermont is a perennial favorite among visitors to the New England region. Towns like Dorset and Woodstock have maintained historic buildings and made social contributions toward a better society. Brattleboro and Manchester hold out museums whose interest and relevance for visitors extend well beyond their local contexts. Other places, like Rutland and Stowe, offer skiing and snowboarding and have left their mark on global wintertime athletics. And not least, college towns rarely get better, or cuter, than Middlebury's quaint campus. For more adorable towns amid beautiful natural scenery, Vermont warrants a first—or latest—visit in 2025.
