15 Most Charming Small Towns in Vermont

An exemplary New England state, Vermont is a wonderland of wilderness. On the border with Canada, this relatively small state is characterized by its beautifully rugged terrain. Mountains boast excellent places to ski and have even produced Winter Olympians.

Hiking and mountain biking trails zigzag through those same areas for summer fun. Lakes fringed by forests offer up glassy pools for hazy, relaxing days. And all the while a history of the early American colony, and the United States, unfolds in Vermont’s small towns – in their museums, monuments, and storied old buildings.

15. Bennington[SEE MAP]

This historic Vermont town is near the site of a major battle in the American War of Independence, and today you can see evidence of that at the Bennington Battle Memorial. This 93-meter obelisk was completed in 1889 and commemorates the 1777 battle itself. It is, in fact, the tallest man-made structure in the whole state!

Nearby is the Park-McCullough Historic House, one of the best-preserved examples of Victorian architecture in the New England area. This 35-room mansion is open to the public, too. The downtown area of Bennington is also awash with historic buildings, pointing back to the original settlement of this town over 250 years ago.

14. Warren[SEE MAP]

The tiny town of Warren is set in the Mad River Valley among two ranges of the lush Green Mountains. Skiing has been popular in the area since the 1930s, when the first ski lift was built in the valley.

Following the development of ski resorts in the 1950s, the town started attracting all sorts of jet set names – including the Kennedys – to holiday on the slopes. During the hot summer months, locals and visitors alike can enjoy cooling off at Warren Falls; this natural swimming spot is a crystal-clear gorge surrounded by the beauty of the mountains.

13. Middlebury[SEE MAP]

Set in Addison County, Middlebury is a good place to come to learn about the history of Vermont. The Henry Sheldon Museum of Vermont History, founded in 1882, is a compact but comprehensive collection of art and antiques. Similarly, the Vermont Folklife Center in town is great for learning all about the culture of Vermont.

Middlebury, aside from its history and historic buildings, is situated near the serene Lake Dunmore – a forested area set around a lake that’s ripe for biking and hiking. Closer to town is the less adventurous Battell Park, which is perfect for a stroll surrounded by nature.

12. Waterbury[SEE MAP]

Waterbury is nestled among the beauty of the Green Mountains in the center of Vermont. There’s plenty to see and do in the town for fans of outdoor activities. Winter months bring the chance to hit the fresh powder and try out skiing or something a little different such as snowshoeing, dog sledding, and sleigh rides.

With the arrival of Spring, the Green Mountain Forest attracts keen campers and hiking enthusiasts to the area. It isn’t just about nature here: it’s also where you can sample Vermont’s locally made produce. Stop off for a refreshing drink at the Cold Hollow Cider Mill or the Green Mountain Coffee Shop; where you can sample the world-famous Ben & Jerry’s Ice Cream in the local factory.

11. Burke[SEE MAP]

The town of Burke is known for its proximity to Burke Mountain: a 1,000-metre-tall peak where you find good skiing in winter – thanks to the Burke Mountain Ski Area – and great hiking in summer.

The mountain biking trails, maintained by volunteers, also become perfect for cross-country skiing in the winter, too. Swimming in the nearby Lake Willoughby and Lake Crystal is fantastic when the weather’s fine in the warmer months, whilst there’s even more outdoor fun to be had in the form of hiking around Mount Hor and Mount Pisgah.

10. Hartford[SEE MAP]

Made up of the five villages of Hartford, Quechee, West Hartford, White River Junction, and Wilder, the town of Hartford was founded in 1971. Located on the confluence of the White River, the Connecticut River, and the Ottauquechee River, which runs through the town, much of history life in the area is based around the three rivers.

The mills which were built along the waterways bought industry to the area in the 19th century and the railways followed suit. Today Hartford is connected to New York by the daily Amtrak Vermonter train, which brings visitors to enjoy the simple local charm.

The town is busy with small independent businesses and museums where you can learn more about the area, like the Main Street Museum, and the Northern Stage Theater.

9. Weston[SEE MAP]

The town of Weston, located in Windsor County, is a place to visit in Vermont for some good old-fashioned charm. Here you can simply stroll around town and lose yourself in its quaint prettiness, from the town green and the Old Parish Church, built in 1832, to the cozy Village Green Gallery where you can enjoy art alongside a coffee.

The clapboard Inn at Weston, dating back to 1848, is a sweet little place for a hearty breakfast, or else you could take yourself to the Weston Priory – home to a small community of Benedictine Monks who sometimes put on services for the public in the small chapel.

8. Waitsfield[SEE MAP]

Waitsfield is surrounded by green fields dotted with old farmhouses in a valley sandwiched between the Green Mountains and the Northfield Mountains. A friendly local town, the area was built up around agriculture and sees many visitors who come to the area to enjoy nearby skiing. As such, many of the 19th century farmhouses have been turned into family fun B&Bs where guests can relax among the beauty of the surrounding nature.

Waitsfield also has a fantastic selection of eateries, from Mexican cuisine, to vegetarian fare, and even a French restaurant; there’s even a locally brewed IPA to wash all of that delicious food down with.

7. Shelburne[SEE MAP]

Shelburne is located on the shores of the sizeable Lake Champlain: 514 square miles of glassy water that spills over the border into neighboring Quebec, Canada. If nothing else, this lakeside location makes for some divine sunsets. But, naturally, Lake Champlain is perfect for watersports, yachting, and simply dipping your toes into the water at the beach – all best enjoyed in the summer months, of course.

Notably, this town is home to the Shelburne Museum, a large space filled with everything from impressionist paintings to Americana curios. Here you can even explore a historic steamboat, one of only two remaining side-paddle-wheel passenger steamers remaining.

6. Stowe[SEE MAP]

Set amidst the Green Mountains, Stowe is well known for being a ski resort thanks to its location close to the highest peak in Vermont, Mount Mansfield. The 19th century town is a picturesque place to spend time exploring; the streets of its Downtown area are home to buildings that have been serving the community for generations.

There’s the iconic white steeple of the Stowe Community Church, which dates back to 1963, and the General Store has been in operation since 1895, as well as the impressive Stowe Theater Guild. After all of that exploring, make sure to stop off at Stowe Public House for some locally brewed beers.

5. Grafton[SEE MAP]

Grafton, considered one of Vermont’s prettiest towns, got its name in a unique way. Originally known as Thomlinson, the right to rename it was auctioned in 1791 for $5 and some rum; the winning bidder named it after his home town of Grafton, Massachusetts. Grafton owes its graceful beauty in part to the private Windham Foundation, which was established in the 1960s to help restore the village.

The foundation’s initiatives included burying all electrical and telephone lines, which helps account for Grafton’s lost-in-time appearance.

4. Dorset[SEE MAP]

Instrumental in the founding of the short-lived Vermont Republic, the town of Dorset dates all the way back to the late 17th century. It is also home to the oldest marble quarry in America.

Some of the stone quarried here was even used in the construction of the New York Public Library. However, the Dorset Quarry has since closed; but it doesn’t remain unused. In the summer, this is a popular swimming hole, with multiple spots to jump in from. There are numerous hiking trails abound in the surrounding area, too. The nearby Dorset Mountain is another great spot for anybody seeking a slice of the outdoors.

3. Woodstock[SEE MAP]

Woodstock boasts more than just historic buildings; it’s also home to the Marsh-Billings-Rockefeller National Historical Park, a leafy slice of nature that’s just asking to be strolled around.

Within the park, you’ll find the Billings Farm and Museum, a progressive dairy farm dating back to 1890 and once owned by Laurance Rockefeller. Nevertheless, there are numerous heritage buildings to marvel at back in town. In fact, the Woodstock Village Historic District features many examples of buildings, like the Norman Williams Public Library, that dates all the way back to the late 18th and 19th centuries.

2. Chester[SEE MAP]

The little town of Chester is a good spot for anybody seeking a quaint slice of New England; the main street here is lined with pretty, historic shops and houses, making for a good day of strolling, browsing, and eating.

The town’s heritage can be seen in some of the more notable structures, like the handsome Old Train Station, or the collection of buildings at the Stone Village; Chester, after all, dates back to 1761.

Numerous annual festivals, like the Big Buzz Chainsaw Carving Festival, the Chester Fall Festival, and the Winter Festival, make it a fun, interesting place to visit any time of year.

1. Manchester[SEE MAP]

With its pretty steeples and historic buildings, Manchester is just about as charming as it gets. And whilst the town captures your heart with buildings like Bennington County Courthouse and Hildene – The Lincoln Family Home (former summer home of Abraham Lincoln’s first son), there’s much more to do than just admiring the architecture.

Nearby Bromley Mountain is perfect for skiing in the winter, but in summer adrenaline junkies should head here for one of the longest ziplines in the state. The nearby Green Mountain National Forest is just under four hundred thousand acres of unadulterated wilderness for hikers, bikers, and strollers alike.