Aerial view of Stowe, Vermont, and the Green Mountains with autumn colors.

7 Delightful Towns to Visit in Vermont

Vermont is a state in the far northeast of the United States that, remarkably, does not border the Atlantic Ocean. However, this landlocked state does not slump when it comes to natural beauty and worthwhile tourist destinations. With its small population and abundance of parks and other natural conservation areas, any trip here is sure to be filled with pristine views in all directions.

Finding a place to stay is important, as you can easily spend days or even weeks in the Green Mountain State, so here are 7 of the most delightful towns that we suggest you stop at during your travels.

Woodstock

Early autumn foliage scene of houses in the mountains of Woodstock, Vermont.
Early autumn foliage scene of houses in the mountains of Woodstock, Vermont.

Woodstock, Vermont, is one of those quintessential New England towns that features a mix of abundant natural beauty away from the cities with historic charm in its downtown district. The Green, an area that sits at the center of town, is surrounded by beautiful 19th-century buildings and serves as a central gathering spot for visitors and residents alike. Nearby, you can explore the Woodstock Inn, an excellent place to spend the night, and take a walk along the local pathways hugging the Ottauquechee River.

The Billings Farm & Museum is perhaps the best destination to learn more about this central Vermont town, giving you a look into the region’s early agricultural roots, while the Marsh-Billings-Rockefeller National Historical Park highlights Vermont’s strong legacy of conservation.

The nearby Quechee Gorge, often referred to as Vermont’s Grand Canyon is a must-see, and in the fall, Woodstock becomes a prime destination for leaf-peeping, with colorful foliage lining the streets and hillsides around town- a true delight for landscape photographers.

Stowe

Aerial view of downtown Stowe, Vermont, showcasing the New England town’s autumn landscape with fall foliage colors.
Aerial view of downtown Stowe, Vermont.

Stowe is a year-round destination known for many nearby parks and outdoor activities that are available regardless of the season. Nestled in the Green Mountains, this northern Vermont town is probably most famous for the Stowe Mountain Resort, a highly sought-after ski destination that attracts winter sports enthusiasts from across the East Coast.

Stowe’s appeal extends beyond the winter season. The scenic landscapes nearby offer excellent hiking, biking, and even ways to go hot-air ballooning during the summer months. The Stowe Recreation Path, for example, is an idyllic 5.3-mile trail that winds through meadows and forests, awarding its travelers with great views of Mount Mansfield, Vermont’s highest peak.

History buffs can visit the Stowe Historical Society Museum, which provides insights into the town’s past dating back to 1763. Many who come here may be more interested in the Vermont Ski and Snowboard Museum, which has been displaying memorabilia and info about the popular winter sports since 1988.

Manchester

Exterior architecture and beautifully landscaped gardens of Hildene, The Lincoln Family Home in Manchester, Vermont.
Hildene, The Lincoln Family Home in Manchester, Vermont. Editorial credit: Theresa Lauria / Shutterstock.com

Moving to a more southern portion of the state, Manchester is a delightful town that is set against the Taconic and Green Mountains. This town of less than 5,000 residents is home to the Hildene estate, the former summer residence of Robert Todd Lincoln, the oldest son of famed president Abraham Lincoln. This unique historic site gives a detailed look into the life of some of Abraham Lincoln’s closest family members in the years after his death. The estate’s gardens and walking trails are also notable for their immense beauty. Downtown Manchester offers more attractions, like the Northshire Bookstore, a beloved independent bookstore that is a must-visit for all kinds of literature lovers.

For outdoor enthusiasts, the nearby Equinox Mountain is a popular spot for hiking, with rewarding views of the surrounding valleys from atop many of the trails found within it. Lye Brook Falls, a short drive south of town, is another natural draw around Manchester, with an easily accessible trail taking you to the meandering cascade.

Middlebury

Middlebury Falls in Middlebury, Vermont.
Middlebury Falls in Middlebury, Vermont.

Middlebury is a charming college town with an accompanying youthful and academic vibe. Home to Middlebury College, one of the nation’s leading liberal arts institutions, this town features a number of fascinating and inspiring locales, like the Middlebury College Museum of Art. This museum has an impressive collection of works from various periods and regions around the world. For those interested in history, the Henry Sheldon Museum of Vermont History will show you a thing or two about the state's storied past, from its original settlers to its founding in 1791 to modern-day subjects.

Middlebury rests along the scenic Otter Creek, where a picturesque waterfall and a footbridge make for a pleasant walk in nature not too far from the town center. As with many towns on this list, the Green Mountains sit nearby and make for a great local escape from town, with trails, lakes, and other outdoor features to be explored.

Brattleboro

Spring aerial photo of Brattleboro, Vermont, on a partly cloudy day.
Spring aerial photo of Brattleboro, Vermont. Editorial credit: SEALANDSKYPHOTO / Shutterstock.com

Brattleboro is on the banks of the Connecticut River on the border of New Hampshire. It sits also remarkably close to the border of neighboring Massachusetts, making it s town that is easily accessible to many looking to spend some time in Vermont.

The arts scene is thriving here, with the Brattleboro Museum & Art Center regularly featuring contemporary exhibitions, while the town’s other numerous galleries, like the Gallery In the Woods, showcase more local talent.

Brattleboro’s history can be seen up close in its collection of preserved buildings, many dating back to the eighteenth century. The Brooks House, built in 1871, has served as a hub for trade and culture since the late 19th century. The nearby Retreat Farm offers family-friendly outdoor activities and a chance to interact with farm animals, perfect for young families, while the nearby West River Trail provides picturesque opportunities for trail walks and biking along the water.

Brattleboro’s calendar is packed with events, including the annual Strolling of the Heifers parade, which celebrates local agriculture, primarily the prevalence of dairy farms and remarkable cheese makers in the area.

Grafton

The Grafton Village Store in Grafton, Vermont.
The Grafton Village Store in Grafton, Vermont. Editorial credit: Bob LoCicero / Shutterstock.com

Grafton is a truly small town, with a population of less than 700 permanent residents. This community, deep in the lush wilds of central Vermont, is notable for its many 18th- and 19th-century buildings that still stand today, many of which have been carefully restored by the Windham Foundation, an organization dedicated to preserving Grafton’s historic character. The centerpiece of the town is the Grafton Inn, one of the oldest operating inns in the United States, which has welcomed guests since 1801.

Grafton is surrounded by the rolling hills that characterize this remote part of the state, with a scenic countryside that is also filled with many small farms and nature reserves. Nearby Grafton Ponds Outdoor Center provides year-round activities, including cross-country skiing and snowshoeing in the winter, and a network of hiking trails in warmer months.

Grafton is also home to the Grafton Village Cheese Company, where you can sample and purchase award-winning cheeses made with locally sourced milk and using traditional methods.

Chester

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

Chester draws those who are curious about Vermont's past with places like the historic Stone Village. This recognized historic district contains a unique collection of 19th-century granite homes, a testament to Chester's commitment to preserving its roots. Take a walk within this fairly compact area and see what homes in this area from centuries ago were truly like.

Events like the Fall Festival in Chester's central green bring together artists, musicians, and food vendors for a celebration of the region’s culture in perhaps the most beautiful time of year to be there.

The nearby Williams River, where fishing and kayaking are popular, is well worth a visit for some adventure outdoors, while the Chester Town Forest hugs to outskirts of town and gives you a chance to explore the dense wildlands that span miles in each direction.

Plan Your Vermont Escape Today

Vermont’s many small towns offer a delightful mix of history, natural beauty, and warm local charm. From the robust arts scene of Brattleboro to the rural retreat of Woodstock, these seven towns capture the essence of this iconic northeast state. Outdoor adventure, a peaceful and relaxing retreat, or a journey through history are all easily at hand in and around these destinations. The next time you find yourself in the Green Mountain State, refer to this list for inspiration for your trip.

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