15 Most Charming Small Towns in Vermont

Martina Rosado
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Bennington

Bennington is one of the only settlements along the scenic valley of the Southern Green Mountains that boasts a stately skyline. It is a secluded small city with a population of 9,000 and a town center that sits along the banks of the river.

It is one of the oldest towns in Vermont and is best known today as the place where author and poet, Walt Whitman, was raised. The Old Elm School-house is located on the corner of White and Main Streets and is a landmark in town.

Bennington has something for everyone. It’s definitely a place for you to explore all that Vermont has to offer. It has many beauty spots and gorgeous landscapes, so your visit won’t be a disappointment.

Warren

Referred to as the “Crown Jewel of Vermont,” Warren is a small country town that is nestled in an area of stunning beauty. It’s a popular tourist destination and is considered the “gateway to the Franklin County countryside.”

Warren is located off Route 10 in southern Vermont. It was established in 1765, and it is home to 1,600 residents. It’s also the political and spiritual center of the entire town.

There are many activities and things to see and do when visiting Warren. Several of these include the St. Joseph’s Church, the New England Culinary Institute, the Warren Town Common, the Warren Historical Society Museum, the Queen Anne’s Garden, the Franklin County Courthouse and many others.

The historical society is a great place to visit for any history lovers. There are many more points of interest in Warren.

The New England Culinary Institute allows you to learn all about cooking from experts in the field. The institute is located in the historic Kettell House and is housed in a building that was originally built circa 1790.

Even if you aren’t interested in learning how to cook, improving your knowledge of the subject will be advantageous in many other areas of your life.

Middlebury

Located right off of Interstate 91, this New England town is well connected by road to the rest of the state and the country.

Middlebury is surrounded by the woods and is a popular tourist attraction due to its concentration of many colleges, including the Vermont College of Fine Arts and Bennington College.

The town has a rich history as a popular stopover for the Underground Railroad. It was known as an ideal place for free spirits, political activists and idealistic thinkers, which is why it was a popular destination for the likes of Henry David Thoreau and Amelia Earhart.

A quaint walkway lined with brick buildings and shops, a peaceful – and free – central park, and an adorable covered bridge make this charming town a welcoming addition to a visit in Vermont.

Waterbury

This small town is located in the northeast corner of Vermont and is close to the Massachusetts state border. There are limited public attractions available, but it is perfect for those seeking a quiet place to live or visit.

Burke

Vermont.

Burke is a town along the Connecticut River, just below the town of Derby, Vermont. The population was only 85 as of the 2010 census. Burke, along with Derby, Corinth, Rockingham, Roxbury, and West Derby are the historic towns in central Vermont.

Expansions have caused the number of residents to drop to 87. This town in Vermont is “the gateway to the northern stockbreeding country,” – the largest ranches are in the towns of Burke and Roxbury.

Elmersville, New York is located in the neighboring town of Rockingham. Burke is called “the gateway to the Rockingham Plateau”.

The beautiful winding Burke River flows through the town with many small and large waterfalls. The population of Burke residents is engaged in dairy farming, and the land around the town is crisscrossed with dirt roads.

Like all small towns with great weather throughout the year, lots of good hunting, and waterfalls, Burke has a lot to offer and numerous bed and breakfasts.

Hartford

Weston

Vermont.

If you’ve ever seen a flashback scene on a television show, you’ve seen Weston, Vermont. Today, the rural town is an ideal spot for the quintessential American small-town experience.

From the small downtown to the area’s many charming B&Bs, ancestry sites, and farm markets, coming to Weston is like traveling back in time.

With a population of just over 1,000, the town is also home to a number of charming, historic buildings in the T-shaped Main Street. These include the historic train depot and the Glove Shop.

On the first Sunday of every month, a popular flea market in the downtown square draws in both locals and visitors from throughout the region.

Although it is hard to stop in Weston and not be charmed, the town has even more to offer visitors other than the unique character of its Main Street.

At 4 miles from the center of Bethel, Ticonderoga, and Essex, you can experience all of the town’s charms while lending a helping hand to communities on the northern part of the state. Weston is also an easy commute from nearby overnights such as Glen House, Jericho, and North Haverhill.

Waitsfield

Waitsfield is, at heart, a quiet country town. It's just 8 miles from the mighty Connecticut River, and less than a mile from the Mount Washington train station.

There's a great selection of local shops, filled with local products. For the artsy types, there's the Waitsfield Gallery.

There are lots of great beaches in the area, and there are some great camping options nearby, including Camp Waitsfield, for those seeking a more rustic experience.

Shelburne

Stowe

Vermont.

Stowe, Vermont is a small community in Vermont that offers a variety of activities for both the young and the old.

The charming town of Stowe is nestled in the picturesque Green Mountains of Vermont. It is a town of about 1,500 people, where the average age is around 50 years old.

The first settlers arrived in the mid-1700s and staked a claim to the land used for farming. Stowe’s tranquility is something that is outstandingly unique. The town is only accessible by car or by bike.

A bicycle is the best way to roam through the adorable town, because the streets are literally knife-edges in the summer months.

For those who are looking to take a dip into the snow, Stowe has a variety of options. On a busy day, there are at least seven ski resorts. The average temperature is below freezing during the winter months, and snow accumulates, providing a unique environment for those new to snow activities.

Stowe is a town that doesn’t live up to its hype, because it’s a small town all year round, but is the perfect spot to visit when it’s not the summer.

Grafton

Population: 1,661 Grafton is a town in Windham County, Vermont, United States. The population was 1,661 at the 2010 census. It is the least populous town in the state, but also one of the wealthiest. It was first settled in the early 1780's by Calvin Smith and his family. The town's original name was Smith's Settlement. It had it’s own post office in 1790, but when a post office was set up in Danby, the town became part of that town. Over the next ten years, it became part of Utica, the county seat. The State of Vermont eventually settled the dispute during the Civil War between Gore and Utica by giving Gore a new post office opening on November 1, 1870. The name of the town was once again changed to Grafton in memory of Captain Fitzhugh, who fought in the Revolutionary War.

Dorset

The idyllic village of Dorset is nestled in Vermont’s Northeast Kingdom and the views of Lake Champlain, Vermont golden fields and the Adirondack Mountains make this charming village a great place for a summer getaway.

There are excellent hiking and biking trails that lead to the stunning views of the Champlain Valley. There is an annual Bluegrass Festival held here in May that features five days of great music and fun. There are also events that take place throughout the summer and there are many activities for young people to enjoy throughout the summer months.

There are also a number of good options for dining in the area. The Yankee Diner and the Angel’s Bluff Inn have been around for over 50 years. The Blue Sky Cafe also serves a delicious food menu. The place to go for a snack is Stone’s Tavern.

The Ladd J. Buck Memorial House is an excellent place to stop by and learn about the history of Dorset. It’s a Greek Revival home that has been restored and is now open to the public. There are also a number of excellent shops there as well. The Dorset Historical Society is another great place to check out.

Woodstock

This charming town is located in the northwest corner of Vermont. The town feels truly rural because the state’s northern border is only a few miles away.

The town is a popular tourist destination that features art galleries, cafes, and other fun shopping opportunities. A yearly Woodstock event is the Grateful Dead Week, and thousands of people come to town to attend.

What to Expect in Woodstock

The Woodstock skyline is relatively low-key, with a number of older buildings that add to its charm. This gives it a quieter feel than many of the other Northeast Kingdom towns.

You can also expect to find delightful greenery, a vibrant downtown, and great shopping and dining opportunities. Make sure not to miss The Tunbridge Fair, which is held every year in late August. The festival features classic and contemporary music, classic car and tractor shows, street fairs, and other attractions.

Expect to find classic architecture throughout town: homes that are older but well-maintained and commercial establishments that are relatively new but still maintain classic charm.

Things to Do in Woodstock

The Woodstock Farmers’ Market is a great place to start. The market has everything you need to cook a gourmet meal, and it even includes a butcher’s stand. You can even get small-batch and organic honey there.

Chester

Chester was originally a trading post established by the famous Ethan Allen and associates in 1761. It started out as a trading post, and was later named Chesterfield for a then-American settler. The settlers who bought the land later sold the land, and the town name was changed to Chester.

Chester still carries the charm of an old community with the small tourist industry of local crafts and gift shops. The town was also named to the National Register of Historic Places in 1972. The town has a population of just over 2,000.

Chester is about a 90 minute drive from East Burke. Whether you are just passing through East Burke and want a quick bite or stay overnight, or make a long weekend to explore all of Vermont, come out to Chester and sleep in the Yellow Bricks bed and breakfast.

Manchester

Manchester is a small town in Vermont that is considered one of the most charming towns in the state. Manchester lies in the middle of between two of the state’s most popular attractions, Mount Snow and As Vermont’s largest town, Manchester attracts a large number of visitors and is near the center of the Interstate 4 corridor.

Manchester is set amongst the Green Mountains which are home to more than 6,000 acres of hiking and cross-country ski trails. The town is also a short drive from the north entrance of North Country National Scenic Trail which stretches along the east bank of the Connecticut River for about 40 miles.

Manchester was previously called Manchester Mills and is one of the oldest sites in the state. The city received its former name in support of a local mill manufacturer which was established in 1840 by George W. Noble.

  • Manchester State Forest covers more than 3,000-acres of the Green Mountain National Forest and is home to an extensive network of trails, some of which lead to many state-owned campsites.
  • Manchester Pond, serving as a local water reservoir for Central Vermont’s water supply, is located just outside of the city.
  • The Manchester Colonial Green and the Manchester Museum are located in Manchester.