Vermont is “country town” country. No matter what season it is, people here make the most of the outdoors, indoors, fresh food and live entertainment. The community spirit is alive and well in each of Vermont’s 237 towns, nine cities, five unincorporated areas, and four gores. With only 626,562 people (as of 2014) Vermont is big enough to have thriving communities as well as small enough to have tight knit communities in each place. While every town in Vermont is beautiful in its own way, here are a few places that stand out from the crowd.
- Grafton
Flickr/Ryan Taylor Grafton, now best known for its charm and its cheese, has an interesting story behind its name. Grafton 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.
- Dorset
Flickr/Doug Kerr This quintessential town has well kept, white clapboard houses overlooking an immaculate town green. You can enjoy the peace and quiet as well as fresh mountain air in Dorset.
- Woodstock
Flickr/Jasperdo Founded in 1761, Woodstock is a picture perfect example of Vermont charm. It’s no wonder why visitors from all over come to experience all it has to offer!
- Stowe
Flickr/My Discovery Stowe is a popular destination in every season. From skiing to hiking to destination weddings to stunning foliage, this classic and charming town is not to be missed.
- Windsor
Flickr/Doug Kerr Windsor is known as the “Birthplace of Vermont,” the town is where the Constitution of Vermont was adopted in 1777. History, outdoor recreation, a quaint downtown, unique shopping experiences and more are among some of the attractions that make Windsor a great destination for a visit or a community to consider home.
- Grand Isle
Flickr/Don Shall
Flickr/Chris Gosselin From historic cabins to art galleries, this island town on Lake Champlain is truly stunning.
- Quechee
Flickr/Doug Kerr The Quechee covered bridge is a classic example of the fine craftsmanship of Vermont’s bridges. This bridge was severely damaged by flooding caused by Hurricane Irene in 2011 and has since been rebuilt.
- Craftsbury
Flickr/Larry Lamsa A picturesque country town located in the Northeast Kingdom, with rolling hills, white picket fences and family run farms.
- Island Pond
Flickr/Ben W
Flickr/Sunil Konduri Located in the Northeast Kingdom, the lovely town of Island Pond is also surrounded by incredible scenery.
- Cabot
Flickr/Doug Kerr With scenery like this, it’s no surprise that the town of Cabot produces some of the world’s best cheese.
- Manchester
Flickr/Craig T This bustling town has something for everyone. Manchester is justifiably famous for it’s shopping, too. If you want to find a great deal in a lovely setting, Manchester is your town!
- Brandon
Flickr/Doug Kerr This classic New England town is known as the “Art & Soul” Village of Vermont. Here you can experience the experience the best of two different worlds: a vibrant, walkable center of art galleries, studios, shops, and restaurants, as well as easy access to the best of four-season outdoor activities.
- Chester
Flickr/Don Shall Chester is a quaint town which is centrally located, and in close proximity to several ski areas including Okemo, Stratton, and Killington. Additionally, Chester offers opportunities for bicyclists, boating enthusiasts, great restaurants, comfortable B&Bs, interesting shops, including many antique stores, lovely art galleries, and a tranquil atmosphere.
- Middlebury
Flickr/Jasperdo Middlebury is much more than a college town. With a historic and lively downtown, it is home to a wide variety of shopping opportunities, including one of Robert Frost’s favorite bookstores, the downtown features over ten restaurants, inns, theaters and more - all within a five-minute walk of the Town Green and gazebo.
In your opinion, what other towns should make the list? Do you agree that these towns are both charming and beautiful? Be sure to share your thoughts!
Flickr/Ryan Taylor
Grafton, now best known for its charm and its cheese, has an interesting story behind its name. Grafton 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.
Flickr/Doug Kerr
This quintessential town has well kept, white clapboard houses overlooking an immaculate town green. You can enjoy the peace and quiet as well as fresh mountain air in Dorset.
Flickr/Jasperdo
Founded in 1761, Woodstock is a picture perfect example of Vermont charm. It’s no wonder why visitors from all over come to experience all it has to offer!
Flickr/My Discovery
Stowe is a popular destination in every season. From skiing to hiking to destination weddings to stunning foliage, this classic and charming town is not to be missed.
Windsor is known as the “Birthplace of Vermont,” the town is where the Constitution of Vermont was adopted in 1777. History, outdoor recreation, a quaint downtown, unique shopping experiences and more are among some of the attractions that make Windsor a great destination for a visit or a community to consider home.
Flickr/Don Shall
Flickr/Chris Gosselin
From historic cabins to art galleries, this island town on Lake Champlain is truly stunning.
The Quechee covered bridge is a classic example of the fine craftsmanship of Vermont’s bridges. This bridge was severely damaged by flooding caused by Hurricane Irene in 2011 and has since been rebuilt.
Flickr/Larry Lamsa
A picturesque country town located in the Northeast Kingdom, with rolling hills, white picket fences and family run farms.
Flickr/Ben W
Flickr/Sunil Konduri
Located in the Northeast Kingdom, the lovely town of Island Pond is also surrounded by incredible scenery.
With scenery like this, it’s no surprise that the town of Cabot produces some of the world’s best cheese.
Flickr/Craig T
This bustling town has something for everyone. Manchester is justifiably famous for it’s shopping, too. If you want to find a great deal in a lovely setting, Manchester is your town!
This classic New England town is known as the “Art & Soul” Village of Vermont. Here you can experience the experience the best of two different worlds: a vibrant, walkable center of art galleries, studios, shops, and restaurants, as well as easy access to the best of four-season outdoor activities.
Chester is a quaint town which is centrally located, and in close proximity to several ski areas including Okemo, Stratton, and Killington. Additionally, Chester offers opportunities for bicyclists, boating enthusiasts, great restaurants, comfortable B&Bs, interesting shops, including many antique stores, lovely art galleries, and a tranquil atmosphere.
Middlebury is much more than a college town. With a historic and lively downtown, it is home to a wide variety of shopping opportunities, including one of Robert Frost’s favorite bookstores, the downtown features over ten restaurants, inns, theaters and more - all within a five-minute walk of the Town Green and gazebo.
OnlyInYourState may earn compensation through affiliate links in this article.
