Vermont’s history runs deep, from becoming the first state to abolish slavery in 1777 to playing a vital role in the Revolutionary War through the Battle of Bennington. The Green Mountain State’s legacy is etched into its architecture, village greens, and industrial landmarks. Historic sites like the Vermont State House, the Bennington Battle Monument, and Hildene preserve this heritage. But beyond the museums and monuments, Vermont is home to small towns where the past is still present, in stone villages, covered bridges, and 18th-century inns. Here are ten must-visit historic towns that showcase the state’s enduring charm and significance.
1. Woodstock
Chartered in 1761, Woodstock stands as a testament to early American history and charm. Designated the Shire Town of Windsor County in 1786, it quickly evolved into a hub for entrepreneurs and artisans, later transforming into a sought-after tourist destination with the advent of the railway in the late 19th century.
Visitors are drawn to its well-preserved 18th- and 19th-century architecture, the iconic Middle Covered Bridge, and the picturesque Village Green. The Marsh-Billings-Rockefeller National Historical Park offers insights into America’s conservation history, while the Billings Farm & Museum showcases Vermont’s agricultural heritage . Downtown, the Woodstock History Center delves into local narratives, and the Woodstock Town Hall Theatre, dating back to 1900, continues to host cultural events.
2. Bennington
Chartered in 1749, it’s Vermont’s oldest town and the site of a critical Revolutionary War victory. The 306-foot Bennington Battle Monument towers above the town, honoring the 1777 clash that helped turn the tide against British forces.
But Bennington’s story doesn’t stop at war. Walk through Old Bennington, where narrow streets lead past 18th-century homes and the beautifully preserved Old First Church, gathered in 1762. The poet Robert Frost is buried here, fittingly among the granite and green.
At the Bennington Museum, history and art converge, home to the largest public collection of Grandma Moses paintings and rotating exhibits of regional artifacts. Nearby, covered bridges still span quiet streams.
3. Middlebury
Middlebury, chartered in 1761 and settled after the American Revolution, quickly became one of the state’s most important industrial and educational centers. Located along Otter Creek, the town developed around water-powered mills, stone buildings, and trade routes that connected early Vermont communities.
A major highlight is Middlebury College, founded in 1800. It remains a cornerstone of the town’s identity, contributing to a vibrant downtown filled with bookshops, museums, and historic architecture. The Pulp Mill Covered Bridge, one of the oldest of its kind in the nation, still spans Otter Creek and reflects the area’s early infrastructure.
When visiting, you can explore the Henry Sheldon Museum, the oldest community-based museum in the United States, which offers extensive exhibits on local history and culture. Middlebury’s compact, walkable center makes it easy to enjoy historic inns, original 19th-century storefronts, and scenic views.
4. Manchester
Founded in 1761, Manchester played a key role in southern Vermont’s early development. It served as a county seat and stagecoach hub, later becoming a retreat for wealthy urbanites in the 19th century. Today, Manchester blends its historical foundations with modern appeal, making it a popular year-round destination.
The town’s historic centerpiece is Hildene, the Lincoln family estate. Built by Robert Todd Lincoln in 1905, the Georgian Revival mansion offers guided tours, preserved furnishings, and a working farm. The nearby Equinox Hotel, established in 1769, has hosted presidents and military leaders and remains a symbol of colonial-era hospitality.
Manchester also features the American Museum of Fly Fishing and several 19th-century churches and civic buildings. The marble sidewalks and restored storefronts in the town center reflect a commitment to preservation.
5. Stowe
Stowe grew from a small agricultural settlement into one of Vermont’s best-known destinations after it was chartered in 1763. While today it’s famous for skiing, the village itself has retained much of its 19th-century charm and historic integrity.
Stowe’s walkable downtown features preserved Greek Revival and Federal-style buildings, a classic white-steepled church, and the 1844 Green Mountain Inn. The Stowe Historical Society Museum, located in a restored one-room schoolhouse, offers a closer look at local life over the past two centuries.
One of the area’s most photographed sites is the covered bridge known as Emily’s Bridge, dating to 1844 and wrapped in local legend. The Stowe Recreation Path also gives visitors a scenic view of the town’s historic core and rural landscape.
Though often associated with outdoor sports, Stowe’s rich heritage, architecture, and long-standing inns make it equally appealing for history lovers.
6. Montpelier
Established in 1787 and designated Vermont’s state capital in 1805, Montpelier is the smallest capital city in the U.S. by population, but its historical and political importance far outweighs its size. The town developed around government and commerce, with early settlers drawn to its location along the Winooski River.
The Vermont State House, completed in 1859, remains the centerpiece. With its gold dome and granite façade, it’s one of the best-preserved state capitols in the country. Visitors can tour the building year-round and walk through adjoining historic districts filled with 19th-century homes, churches, and civic buildings.
Montpelier is also home to the Vermont Historical Society Museum, located in a restored 19th-century school, offering exhibits on everything from early settlement to modern legislation.
Unlike other capitals, Montpelier has no fast-food franchises downtown, preserving its independent, small-town feel.
7. Vergennes
Incorporated in 1788, Vergennes holds the title of Vermont’s oldest and smallest city. Named after French diplomat Charles Gravier, Comte de Vergennes, it was founded at the junction of three towns, Waltham, Ferrisburgh, and Panton, strategically located on Otter Creek.
Despite its small size, Vergennes played a major role in American naval history. During the War of 1812, Commodore Thomas Macdonough oversaw the construction of a fleet here at the city’s falls. These ships later contributed to the U.S. victory at the Battle of Plattsburgh in 1814.
Today, the city retains its historic layout and industrial-era architecture. Visitors can view remnants of the Monkton Iron Works and stroll along the restored downtown filled with brick buildings, local shops, and cafés. Nearby, Vergennes Falls Park offers a scenic look at the same waters that once powered its industries.
8. Grafton
Grafton, chartered in 1754, stands as one of Vermont’s best-preserved historic villages, not by accident, but through deliberate restoration. Once a bustling sheep-farming and stagecoach town, Grafton fell into decline by the early 20th century. In the 1960s, the Windham Foundation stepped in, buying and restoring key buildings to revive the town without losing its heritage.
Today, nearly every structure in the village center dates back to the 18th or 19th century. The Grafton Inn, in operation since 1801, has hosted everyone from Ulysses S. Grant to Rudyard Kipling. The town’s blacksmith shop, schoolhouse, and general store all reflect original craftsmanship and local character.
Visitors can explore the Grafton Historical Society Museum, enjoy quiet walking tours, and stop by the Grafton Village Cheese Company, which continues Vermont’s artisanal food tradition.
9. Chester
Chartered in 1754, Chester is a Southern Vermont town best known for its rare collection of 19th-century stone houses. Located along the Williams River, it developed steadily through agriculture, small manufacturing, and as a waypoint between major routes.
What sets Chester apart is its “Stone Village,” a unique cluster of homes built in the 1830s from locally quarried granite. These Greek Revival structures are so distinctive that the area is listed on the National Register of Historic Places. Visitors can take a self-guided walking tour to appreciate the craftsmanship and symmetry of these preserved residences.
Beyond the Stone Village, Chester’s village green is surrounded by antique shops, inns, and galleries housed in buildings dating back to the 18th and 19th centuries. The Chester Depot area, once a railroad hub, still features a historic train station and classic Vermont charm.
10. Brandon
Founded in 1761, Brandon grew into a model 19th-century New England town through planned development and industrial growth. Unlike many villages that expanded organically, Brandon’s layout was shaped deliberately, with a broad main street and structured downtown, elements still visible today.
By the mid-1800s, Brandon was a center for ironworks, marble processing, and manufacturing, powered by the Neshobe River. Over 240 buildings in the town are listed on the National Register of Historic Places, spanning Greek Revival, Federal, and Victorian styles. The town’s cohesive architectural character is a result of long-standing efforts to preserve and reuse its historic core.
Brandon also embraces its creative side. It’s known as the “Art and Soul” of Vermont, with studios, galleries, and public art integrated into everyday life. Birthplace of U.S. statesman Stephen A. Douglas, Brandon balances deep historic roots with a strong sense of civic pride and cultural engagement.
