The 12 Best Small Towns in Vermont

Vermont is one of the smaller states in the United States, but it is teeming with history and culture.

The area was originally settled by English and French, but the English gained full control over the area after the French and Indian War.

The state did not originally join the 13 colonies after the American Revolution. Instead, it remained independent until it became the 14th state in 1790. Today, tourism, agriculture, and manufacturing are just a few of Vermont’s top industries.

If you’re looking to visit Vermont, comparison shop for better auto insurance coverage before hitting the road. Enter your ZIP code above to begin!

Vermont’s History

Vermont is appropriately named the Green Mountain State because of its rolling green hills and snow-capped mountains. There are also gorgeous valleys, plains, and rivers. An abundance of tree species adds beauty to the landscape as well.

Notably, many people visit Vermont in the fall months to admire the stunning beauty of the foliage changing colors.

There are numerous ski resorts throughout Vermont that visitors flock to in the winter. Spring months are usually mild and are ideal for sampling maple syrup. The warm summer climate is perfect for outdoor recreation at local parks.

There is something for everyone to enjoy about Vermont. From skiing at the resorts in the winter or hiking along hilly trails in the summer, you can enjoy an abundance of outdoor recreational activities.

There are also numerous museums, small town shops, factories that offer guided tours, and historic sites to explore.

Vermont even has some exceptional beaches, such as Sand Bar State Park, Bomoseen State Park, Boulder Beach State Park, and others.

One of the best ways to get to know more about Vermont is to take a road trip and explore some of its most popular and charming small towns.

The 12 Best Small Towns in Vermont

#1 — Chester

Population: 3,154
Must See: Chester Fall Festival on the Green, Stone Village Historic District, Chester Village Historic District

Originally founded in 1754 by a charter from a New Hampshire governor, Chester is named after the Earl of Chester, who is King George III’s eldest son.

Chester is known for its incredible architecture, and many of the older homes in this town are made out of granite. They feature Federal, Revival, Colonial, and Victorian styles of architecture.

If you plan to visit the town in September, plan your dates around the famous Chester Fall Festival on the Green.

Any time of year, take the time to tour the historic districts of Stone Village and Chester Village to admire the beautiful architecture of some buildings in Chester that are dated as far back as 1750.

#2 — Woodstock

Population: 3,048
Must See: Billings Farm and Museum, Marsh-Billings-Rockefeller National Historic Park

If you want to enjoy the quintessential small-town Vermont experience, Woodstock is an excellent place to explore.

This town was originally established in 1761, and today, it retains its historic charm with a modern flair.

For example, the town is nicknamed Wireless Woodstock because it offers free community-wide wireless Internet access.

When you visit Woodstock, stop by the historic Billings Farm and Museum, which is a restored dairy farm and farmhouse that was once owned by the Rockefeller clan. Outdoor enthusiasts can spend time exploring the Marsh-Billings-Rockefeller National Historic Park.

There are also numerous art galleries, shops, and restaurants to explore in Woodstock.

#3 — Stowe

Population: 4,314
Must See: Stowe Mountain Resort, Vermont Ski and Snowboard Museum

Situated in northern Vermont, Stowe was chartered in 1763, and it is a booming resort town today.

Stowe is most notably the location of the Stowe Mountain Resort, which offers year-round mountain activities that range from hiking, skiing, and snowboarding to cycling, swimming, gondola rides, and more.

You may also want to tour the Vermont Ski and Snowboard Museum, which has everything from skiing and snowboarding memorabilia and historic items to fine art and cultural exhibits.

Other points of interest in the area include the Trapp Family Lodge, the Pinnacle hiking trail, and the Stowehof.

#4 — Manchester

Population: 4,391
Must See: Factory outlet stores, smaller boutique shops

If you love to shop, you will not want to pass on the opportunity to explore Manchester.

This small Vermont town was founded in 1761, and it retains historic charm in three distinctive historic districts. These are located on Main Street, Highland Avenue at Elm Street, and Bonnet Street.

Manchester is home to factory outlet stores for Ralph Lauren and Brooks Brothers, which will delight shoppers looking for a great deal on quality merchandise.

You can also shop at numerous smaller boutique shops, tour art galleries, and enjoy local cuisine while you are in the area.

#5 — Grafton

Population: 679
Must See: Grafton Pond, Grafton Village Cheese Company

Visiting Grafton is like stepping back in time. Grafton is one of the smaller towns on the list, and its history dates back more than 250 years.

It reached its peak population around the Civil War era, and there has been a resurgence to revitalize the town in recent years.

The town is located ideally between Albany and the Green Mountains, so it receives a significant number of visitors regularly.

If you are planning a visit to Grafton, be sure to stop by the Grafton Village Cheese Company for artisanal cheeses or Grafton Pond to learn more about its outdoor recreational training programs available.

#6 — Grand Isle

Population: 2,067
Must See: Grand Isle State Park, Ed Weed Fish Culture Station, Hyde Log Cabin

Situated in the far northwestern corner of the state, Grand Isle was founded in 1798.

Grand Isle State Park is the most visited state park in Vermont, located on Lake Champlain. Visitors to the state park can enjoy a broad range of activities, including camping, fishing, canoeing, kayaking, hiking, and more.

Another hot spot in Grand Isle is the Ed Weed Fish Culture Station, which is just one of five of these locations in the state. History buffs may also want to tour the oldest log cabin in the state, which is the 18th century Hyde Log Cabin.

#7 — Craftsbury

Population: 1,136
Must See: Craftsbury Outdoor Center, Craftsbury Sculling Center

Craftsbury was established in 1790, and it is comprised of four smaller villages which each have distinct flair and personality.

Craftsbury is a beautiful area with rolling green hills, picturesque farms, and beautiful historic districts.

Because of the Craftsbury Outdoor Center and Craftsbury Sculling Center, it has become a favorite spot for outdoor recreational activities such as snowmobiling, cross-country skiing, and more. Many visitors also enjoy maple sugaring as soon as winter fades away into spring.

If you plan to visit Craftsbury in July, be sure to enjoy the Antiques and Uniques Festival.

#8 — Charlotte

Population: 3,754
Must See: Mount Philo State Park, Charlotte Village Winery

Named after King George III’s wife, Charlotte is a beautiful agricultural community located in the Champlain Valley. Here, you will find farms that produce everything from grain and berries to honey and more.

Many outdoor enthusiasts flock to Charlotte to enjoy time outdoors at the Mount Philo State Park. Camping, hiking, picnicking, and wildlife viewing are popular at the state park.

If you love touring wineries, you will also want to stop at the Charlotte Village Winery for free tastings of Cabernet Sauvignon, Merlot, and more.

#9 — Quechee

Population: 656
Must See: Quechee State Park, covered bridge, Simon Pearce glass blowing facility

Quechee is a unique small town in Vermont that you can visit. Quechee is a very small, unincorporated community that has an abundance of natural beauty.

The Quechee State Park is a popular attraction, and it is home to the Quechee Gorge. Hiking, fishing, camping, and other activities are common at the park.

You can also tour one of the famous covered bridges in Vermont when you visit Quechee.

The Cogan House Covered Bridge is located next to a historic mill. This former mill is now the home of the famous Simon Pearce glass blowing facility, which is open for tours and has a fabulous restaurant.

#10 — Cabot

Population: 1,547
Must See: Cabot Creamery, Molly’s Pond

Situated in north-central Vermont, Cabot is a scenic small town that is largely based on agriculture.

It suffered a tremendous setback during the Civil War when a large portion of its adult male population was killed. A town monument honors the deceased.

Cabot is home to Cabot Creamery, which was founded in 1919 and is well-known for its cheese products. You can tour the creamery when you visit Cabot.

You may also enjoy the more natural surroundings of Molly’s Pond. This pond is named after the wife of the famous and friendly Native American scout known as Indian Joe.

#11 — Middlebury

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Population: 8,496
Must See: Middlebury College, Henry Sheldon Museum of Vermont History

Middlebury is one of the larger towns on the list and notably the hometown of the famous poet Robert Frost.

When you visit Middlebury, you can tour the reputable liberal arts school of Middlebury College. You can also learn more about the history of the state by exploring the exhibits at the Henry Sheldon Museum of Vermont History.

Other popular points of interest in Middlebury include the Trail Around Middlebury, Otter Creek Falls, the Emma Willard Memorial, and Woodchuck Hard Cider.

#12 — Lincoln

Population: 1,271
Must See: Long Trail, Lincoln Gap, Tibetian Buddhist Nunnery

Lincoln is a quaint community that is located just a short drive from Middlebury. Lincoln sits near New Haven River and Mount Abraham, and it is within close proximity to the Sugarbush and Mad River Glen ski areas.

Many people who visit Lincoln do so to explore natural areas, such as the Long Trail and Lincoln Gap in the Cumberland Mountains.

You may also want to bring your camera to photograph some of the stunning landscapes found throughout this area.

Driving in Vermont

With these and other charming small towns to explore in Vermont, you can easily spend several weeks or more driving across the state.

As you travel, there is a possibility that you may be involved in an accident.

You need to have the right car insurance to financially protect you.

– Review Your Coverage

Before you start on your journey, review your coverage to ensure that it complies with state law.

The minimum required coverage in Vermont includes: 

• $25,000 for bodily injury per person or $50,000 per accident
• $10,000 per accident for property damage

– Drive Safely

You can follow a few steps to stay safe while driving on Vermont roadways. For example, in the fall months, avoid breaking on leaves and break carefully on wet roads to avoid sliding.

Always drive the posted speed limit, and be alert for wildlife. Be particularly vigilant at sunrise and sunset when the sun’s glare could decrease visibility.

If you are driving in Vermont in the winter months, check the tread on your tires before you venture out, and stock your car with extra blankets, an emergency kit, and food supplies in case you get stranded.

– Know What You Want

When you are shopping for new car insurance rates, it is best to analyze your specific coverage needs before requesting quotes.

Remember that state coverage requirements are minimums, and many drivers prefer to purchase more than the minimum amount required by law.

Comparison shop online to find the best deals with fast results.

While your goal is to save money, you should also learn more about the financial strength and the overall industry reputation of the provider before you finalize your decision.

Enter your ZIP code below and compare at least three to four auto insurance policies today!