6 Small Towns in Vermont With Big Charm

It’s an often-overlooked fact that the beautiful state of Vermont was once an independent nation, complete with its own army, post office…  even its own currency. This independent streak lasted only 14 years before the “Green Mountain State” signed up to become the 14th state to join the Union in 1791.

Since then, Vermont has played an important role in the history of the United States with its many small towns serving as a backdrop not just to crucial events, but also as homes to some of the most welcoming populations in the country. Find out more about these must-visit communities with our list of six small towns in Vermont with big charm.

Woodstock

The charming small town of Woodstock is located in Vermont’s picturesque Green Mountains and looks every inch like the kind of quaint New England community you’d see in a painting. Tourists and photographers also love Woodstock for its cultural richness and historical significance. Topping the list of fun things to do in Woodstock is to pay a visit to Marsh-Billings-Rockefeller National Historical Park, a one-of-a-kind attraction focusing on conservation history and the evolving nature of land stewardship. Once home to George Perkins Marsh, one of America's first conservationists, you’ll want to tour the old home and gardens here.

You’ll also want to include the Billings Farm and Museum on your Woodstock itinerary. This fully operational dairy farm doubles as a museum of Vermont's rural past with interactive experiences that highlight 19th-century farm life. Be sure to also visit downtown Woodstock for its well-preserved Federal, Greek Revival, and Victorian-style architecture, as well as the town’s covered bridges, particularly the Middle Bridge.​ Top your trip off with a stay at the charming Woodstock Inn & Resort.  

Manchester

Manchester is another Green Mountains destination known for its charming small-town feel. A key attraction in Manchester is Hildene, the historic estate of Robert Todd Lincoln, the only child of Abraham Lincoln to survive into adulthood. In addition to the mansion, you can also explore the property’s formal gardens, a restored 1903 Pullman car, and also enjoy a network of hiking trails. Book lovers should make a beeline for the famous Northshire Bookstore to pick up something to read about the Lincoln family and their influence in Vermont.

Outdoor activities are also plentiful in the area, with Stratton Mountain Resort being especially popular in winter for its ski slopes. Hiking is also popular with the Prospect Rock Trail, Appalachian Trail, and Lye Brook Falls Trail being among the best.

Chester

Situated in Windsor County near the state border with New Hampshire, Chester’s at its most charming once the snow flies. A visit to Chester places you near several winter sports areas including Okemo Mountain Resort, Bromley Mountain Ski Resort, and Stratton Mountain Resort, all of them popular skiing and snowboarding destinations. Warmer weather visits will enable you to enjoy activities including hiking and mountain biking.

Chester is also known for its beautiful architecture and historical sites, with standouts including the charming Chester Green with its well-preserved architecture (it’s also home to the Chester Festival on the Green is a fun event that showcases an array of local artistic talents held each September). This charming small town is also a stop for the Green Mountain Railroad, a 50-mile scenic tourist train ride that’s especially fun in autumn when the fall colors arrive.

Grafton

Just a 10-minute scenic drive south of Chester and you’ll find yourself in the tiny community of Grafton, home to just 650 residents. More a village than a town, charming Grafton is often included on lists of the prettiest places to visit in New England, and for good reason. Founded in 1754, a visit to Grafton reveals a treasure trove of history, including the Grafton Inn.

Established in 1801, this historic hostelry has hosted many distinguished guests over the years, including Presidents Theodore Roosevelt and Woodrow Wilson. The inn’s postcard-worthy appearance is heightened by the surrounding heritage homes, an authentic general store, and the attractive Grafton Community Church, built in 1875. Also worth a visit is the nearby Grafton Historical Society, a small yet interesting museum that offers insights into the town's past.

Brattleboro

Tucked away in the southeast corner of the state and close to both New Hampshire and Massachusetts, Brattleboro’s picturesque setting in the Connecticut River Valley is a big draw for creative types and outdoor enthusiasts alike. A great time to visit is during the quirky Strolling of the Heifers, a delightful event that celebrates the town's agricultural heritage and its community spirit. Held each June, the stars of this fun family-friendly event are the many calves paraded through downtown Brattleboro, often in crazy costumes and proudly displayed by local farmers.

Another notable Brattleboro attraction is the Creamery Covered Bridge. Now for use only by pedestrians, this picturesque historic landmark was built in 1879 and is a popular spot for selfies.

Shelburne

Located just south of Burlington on the east shore of Lake Champlain, a beautiful body of water which it shares with neighboring New York State, Shelburne is well-known as the home to the must-visit Shelburne Museum. This fascinating attraction is spread across a 45-acre campus and houses an extensive collection of American art and design, including impressive collections ranging from impressionist paintings to Americana. Other highlights include a historic steamboat, the Ticonderoga, one of the last surviving side-paddle-wheel passenger steamers. Though now on dry land, it can be toured.

Another great spot to explore is Shelburne Farms, a working farm and educational center focusing on sustainable agriculture. You can tour the farm, learn about sustainable farming practices, interact with animals, and also enjoy fun cheese-making workshops. Interested in maritime history? Then be sure to pop into the Lake Champlain Maritime Museum with exhibits relating to the lake’s history and an impressive collection of historic ships and exhibits on underwater archaeology.

The Final Word

For travellers seeking an authentic and immersive Vermont travel experience, you can’t do much better than spend time exploring some of the Green Mountain State’s most attractive small towns. From the historic landmarks of Woodstock to the sometimes-cattle-filled streets of Brattleboro, each of the towns in our list of 6 small towns in Vermont with big charm is well worth including on your New England travel itinerary. You can also find out more through the state's official tourist website, Visit Vermont.