The name Vermont often invokes visions straight out of a Norman Rockwell painting, and luckily we have been able to maintain much of that picturesque charm today. America is made up of small towns, and lucky for us, Vermont is chock full of them. Small towns are sometimes overlooked, yet often provide the greatest insights into local culture and enable travelers to engage with locals in uncommon ways.  Be prepared to drive to these towns, since the best places are typically off the beaten path, but this will allow you to explore Vermont at your own pace and enjoy every bit. Here are 17 picturesque small towns in Vermont that are absolutely delightful.

1. Woodstock
Flickr/HBarrison
Flickr/DevonshireMedia
With its picturesque village, unique shopping and plenty of dining options, Woodstock is a popular tourist destination giving people the chance to experience Vermont’s small town charm all in one place. Pictured above is part of the Billings Farm and Museum which is a National Historic Landmark, and its land and mansion were owned by Laurance Rockefeller and his wife Mary French Rockefeller. The farm and museum include an operating dairy farm and a restored 1890 farm house, also pictured is a charming country store.

Read more about it right here.
2. Grafton
Flickr/girl_named_fred
Flickr/aussiegtl
Grafton, now best known for its charm and its cheese, was originally founded as Thomlinson, but renaming rights were auctioned in 1791. The high bidder, who reportedly offered "five dollars and a jug of rum," changed the name to Grafton after his home town of Grafton, Massachusetts. Possibly as a result of having celebrated a bit too much with the rum (some say it was hard cider), the money was never collected, but the new name remained.

Read more about it right here.
3. Putney
Flickr/Putneypics
It may be small, but boy is it mighty. In 2006, Putney passed a resolution endorsing the impeachment of President George W. Bush.

Read more about it right here.
4. Grand Isle
Flickr/.erin.
According to the United States Census Bureau, Grand Isle has a total area of 35.1 square miles of which 16.5 square miles is land and 18.6 square miles is water. Also, in 2009 Grand Isle was the last town in Vermont to adopt a school budget.

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5. Stowe
Flickr/ Jim Liestman
Stowe is host to arts and crafts shows, a balloon festival, British Invasion and many other special events. Along with the Stowe Theater Guild, Ski and Snowboard Museum and the Trapp Family Lodge, Stowe is also home to Mount Mansfield which is Vermont’s highest peak. With all this to offer, along with the village charm of a small town, it’s no wonder people from all over come to experience Stowe.

Read more about it right here.
6. Charlotte
Flickr/fmurphy_nyc
Charlotte has the remote, small town charm, but is still close to Burlington which gives it the best of both worlds. Charlotte is home to 990-foot-high Mount Philo which is in the state's first and most frequently visited state park. The park was established in 1924 and is open seasonally.

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7. Quechee
Flickr/BFS Man
With a population of just over 600, Quechee is the site of Quechee Gorge on the Ottauquechee River and is also the home to the Quechee Lakes. It may be best known for a picturesque covered bridge at the site of the old Quechee mill, which now houses the Simon Pearce glass-blowing facility and restaurant. The bridge was severely damaged by flooding caused by Hurricane Irene in 2011 and has since been rebuilt.

Read more about it right here.

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8. Cabot
Flickr/dudegeoff
Quintessential Cabot contains several ponds and dairy farms and is the headquarters of the Cabot Creamery, a producer and national distributor of dairy products including its world famous cheddar cheese.

Read more about it right here.
9. Craftsbury
Flickr/Sterling College
Craftsbury Common (pictured above) is a beautiful place all year long, but especially on an October morning. Originally, North Craftsbury was settled by the earliest pioneers, and was for many years the center of business and trade, not only for Craftsbury, but for Eden, Lowell, Albany, and portions of the neighboring towns. Continuing trouble with American Indians led to the successive founding of Craftsbury Village (in a valley), East Craftsbury (on higher ground) and Craftsbury Common (on a hilltop).
10. Manchester
Flickr/DevonshireMedia
Manchester Village is an incorporated village, and Manchester Center are settlement centers within the town itself. Pictured is the Manchester version of a "strip mall."

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11. Plymouth
Flickr/Dougtone
The population of the small town of Plymouth was 619 at the 2010 census and Plymouth was home to Calvin Coolidge, the 30th President of the United States. Coolidge was born and reared in Plymouth and is buried there as well. The State of Vermont Division for Historic Preservation owns and maintains the Coolidge Homestead and the village of Plymouth Notch. Plus, you can get some great artisan cheese here.

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12. Rockingham
Flickr/aussiegtl
Despite being on the larger side of small-town Vermont, Rockingham has no formal town center. Instead, its town offices and the Rockingham Public Library are located in the village of Bellows Falls, and the listed center of town is on Route 103, the location of the Rockingham Meeting House.

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13. Chester
Flickr/oragamidon
Chester is famous for its Stone Village Historic District and Chester Village Historic District, and both districts are listed in the National Register of Historic Places. The Stone Village section is known for the many houses made of local granite. The Chester Factory Village has homes that were built between 1750-1924, and includes Victorian, Colonial Revival and Federal style architecture.

Read more about it right here.
14. Royalton
Flickr/Ken Lund
Royalton is located on the east side of the Green Mountains with the White River cutting through its center. Vermont Law School, the state's only accredited law school, is located in South Royalton. You'll find one of our favorite restaurants here, too.

Read more about it right here.
15. Barnet
Flickr/US Department of State
Ocean explorer and scuba inventor Jacques Cousteau had influential experiences on Barnet’s Harvey's Lake as a young boy in the early 1920s. While attending a summer camp he experimented with staying underwater by breathing through hollow reeds found in the lake shallows. Though he could not yet swim well, this allowed him to stay underwater for extended periods.

Read more about it right here.
16. Middlebury
Flickr/oragamidon
Middlebury may be on the larger side of small towns, but it still has the picturesque charm that people envision when they think of picture-perfect Vermont. Middlebury is home to Middlebury College and the Henry Sheldon Museum of Vermont History. There are fascinating ruins in the middle of town, too!

Read more about it right here.
17. Lincoln
Flickr/Carly & Art
Like many towns in Vermont, Lincoln is rich in history, however it may be best known today for its treehouse. The treehouse is a unique and cozy little place perched on four maples 30 feet above a blanket of ferns and available for nightly rental starting at $149 per night. This isn’t your traditional, rustic treehouse. Here you’ll have a private bathroom with shower, heat, electricity, and a small refrigerator.

What is your favorite picturesque town in Vermont? Let us know and have fun exploring the Green Mountain State.

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More to Explore

picturesque small towns in Vermont

Kim Magaraci | March 10, 2021

What is Vermont known for?

First and foremost, the Green Mountain State is known for being absolutely beautiful. With small towns and villages, rolling hills, gorgeous mountains, and sprawling lakes, it's hard to imagine any better scenery anywhere else! On top of that, Vermont is known for its food. World-famous cheddar cheeses, outstanding maple syrup, and ice cream that comes from our creameries and farms are just a few of the delicious treats you'll find up here. You'll also find plenty of outdoor recreation, and Vermont is known for having the best ski resorts in the East.

Where is the best place to live in Vermont?

Vermont is lucky to have so many small communities that make for great home towns! In Norwich, it seems like everyone knows their neighbors. In Charlotte, gardens and great schools draw families to enjoy town. Williston offers close proximity to Burlington's amenities while still maintaining that rural town feel.

What are the most beautiful places in Vermont?

Lake Champlain is an iconic body of water that's frequently called the most beautiful place in Vermont. We're also partial to Brattleboro's charming wildflowers and covered bride, the scenic Mad River area in Fayston, Green Mountain National Forest, and the ski areas like Stowe, Killington, Mount Snow, and Smuggler's Notch.

 

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Featured Addresses
Woodstock, VT, USA
Grafton, VT, USA
Putney, VT 05346, USA
Grand Isle, VT 05458, USA
Stowe, VT 05672, USA
Charlotte, VT 05445, USA
Quechee, Hartford, VT, USA
Cabot, VT 05647, USA
Craftsbury, VT, USA
Manchester, VT 05255, USA
Plymouth, VT, USA
Town of Rockingham, VT, USA
Chester, VT 05143, USA
Royalton, VT, USA
Barnet, VT, USA
Middlebury, VT 05753, USA
Lincoln, VT 05443, USA