Here Are The Most Beautiful, Charming Small Towns In Vermont

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. These are, in our opinion, the best towns in Vermont!

Grafton, VT, USA

Flickr/Ryan Taylor

Grafton, Vermont, which is 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 hometown 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, VT, USA

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 beautiful Dorset, Vermont.

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Woodstock, VT, USA

Flickr/Jasperdo

Founded in 1761, Woodstock, Vermont 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!

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Stowe, VT 05672, USA

Flickr/My Discovery

Stowe, Vermont 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. Once you've visited, we are sure you will agree that it's one of the best towns in Northeast Kingdom, Vermont.

Windsor, VT 05089, USA

Flickr/Doug Kerr

Windsor, Vermont is known as the "Birthplace of Vermont," where the Constitution of Vermont was adopted in 1777. History, outdoor recreation, a quaint downtown, and unique shopping experiences are among some of the attractions that make Windsor a great destination for a visit or a community to consider home. Lots of people think of it as one of the best day trips in Vermont!

Flickr/Don Shall

Grand Isle, VT 05458, USA

Flickr/Chris Gosselin

From historic cabins to art galleries, this island town on Lake Champlain is truly stunning. Grand Isle, Vermont is quite aptly named! It is full of beauty and definitely grand.

Quechee, Hartford, VT, USA

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. It is certainly worth a visit to Quechee, Vermont to see it for yourself!

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Craftsbury, VT, USA

Flickr/Larry Lamsa

A picturesque country town located in the Northeast Kingdom, Craftsbury, Vermont is bound to capture your heart. You will love the beauty and charm of the rolling hills, white picket fences, and family-run farms found in this little paradise. If you're looking for quaint towns in Vermont, this one is an excellent choice.

Flickr/Ben W

Island Pond, Brighton, VT 05846, USA

Flickr/Sunil Konduri

Located in the Northeast Kingdom, the lovely town of Island Pond, Vermont is also surrounded by incredible scenery.

Cabot, VT 05647, USA

Flickr/Doug Kerr

With scenery like this, it's no surprise that the town of Cabot, Vermont produces some of the world's best cheese.

Manchester, VT 05255, USA

Flickr/Craig T

This bustling town has something for everyone. Manchester, Vermont is justifiably famous for its shopping. If you want to find a great deal in a lovely setting, Manchester is your town!

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Brandon, VT 05733, USA

Flickr/Doug Kerr

This classic New England town is known as the "Art & Soul" Village of Vermont. Here in pretty Brandon, Vermont, you can experience the best of two different worlds: a vibrant, walkable center of art galleries, studios, shops, and restaurants, and easy access to the best of four-season outdoor activities.

Chester, VT 05143, USA

Flickr/Don Shall

Chester, Vermont is a quaint town that is centrally located and in close proximity to several ski areas, including Okemo, Stratton, and Killington. Additionally, Chester offers opportunities for bicyclists and boating enthusiasts, great restaurants, comfortable B&Bs, interesting shops, including many antique stores, lovely art galleries, and a tranquil atmosphere.

Middlebury, VT 05753, USA

Flickr/Jasperdo

Middlebury, Vermont is much more than a college town. There are so many fun things to do in Middlebury, Vermont. 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 area 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!