The Green Mountain State is well known for its picturesque towns, many of them containing some of the best downtowns in VT. The main streets (often aptly named Main Street) often have grand architecture, eclectic small businesses, and community-oriented features like a park or theater. Often, these main streets in VT thrive thanks to locals who have made a conscientious effort to fight the general decline of main streets. Here are some of best towns in VT to visit.

1. Montpelier
Montpelier, VT 05602, USA
Flickr/calmer
Montpelier is the smallest capital city in the country and it has one of the best downtowns in VT. Here, you'll find farm-to-table restaurants, book shops, a record store, and much more. In the summer, there are daily farmers’ markets, too. Learn more about what you can do in Montpelier.
2. Woodstock
Woodstock, VT, USA
Flickr/davidwilson194
Woodstock is often referred to as the quintessential Vermont town by travel guides and magazines. This historic village is full of charm, is impeccably maintained, and is one of the best shopping towns in VT. Forget about finding any national chain stores in town; the shops, boutiques, and restaurants are locally owned. You won’t find a Bed Bath and Beyond or Barnes and Noble here, folks. Instead, there’s Yankee Bookshop, F.H. Gillingham & Sons, and The Woodstock Inn and Resort, which provides the perfect home base for strolling adventures. Check out this article for more info on Woodstock and what it has to offer.
3. Burlington
Burlington, VT, USA
Flickr-AX-
The Church Street Marketplace is a great place to wander. You can find anything on this street from a distillery, quaint clothing shops, chocolate shops, pubs, gifts, tea, coffee, and plenty of food choices. The giant Christmas tree is spectacularly lit at the top of the street throughout the holiday season. All this makes Burlington one of the best towns in VT. Get all the details on visiting Burlington.
4. Bristol
Bristol, VT 05443, USA
Flickr/Jasperdo
One of the best downtowns in VT, the entirety of Bristol's is a National Historic District, so step back in time and explore the friendly village shops. Your choices will include art, home accessories, gifts, vintage collectibles, books, toys, clothing, and Vermont products. The dining options are aplenty, too! Bristol loves festivals and they have one of the best July 4th celebrations in the state. And when the weather is warm, there's also a pretty awesome VT swimming hole here.
5. Bennington
Bennington, VT 05201, USA
Flickr/Dougtone
A great place to get your blood flowing with a stroll is around the VT main street of downtown Bennington. From The Saint Francis De Sales Church to old mills to the Bennington Bookshop to The Chocolate Barn to The Sugar Shack, you’ll find exactly what you’re looking for (and more)! There's also some history here, too! Learn about Bennington's Revolutionary War history.
6. Ludlow
Ludlow, VT 05149, USA
Flickr/Dougtone
Ludlow is a small village surrounded by wooded hills and located at the base of Okemo Mountain. There is plenty to do all seasons of the year, and in the heart of Ludlow there are about five blocks of shops and restaurants on Main Street. It's one of the best shopping towns in VT and perfect for a stroll when the weather is nice. Find more reasons why Ludlow should be on your list of places to visit in Vermont.
7. Manchester
Manchester, VT 05255, USA
Flickr/mava
Manchester, with its gilded mansions and upscale factory outlets, draws more shoppers than ski bums. But this rural town in the southern Vermont Valley offers more than just high-end retail stores. Manchester is full of local arts-and-crafts shops and artisanal restaurants, making it one of the coolest towns in VT. Get all you need to know about visiting Manchester.

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8. St. Johnsbury
Saint Johnsbury, St Johnsbury, VT, USA
Flickr/ J. Stephen Conn
St. Johnsbury, or rather "St. J," as it's known to its residents, is the hub of the Northeast Kingdom. One of the best downtowns in VT, this one is a classic New England original with late 19th-century Victorian homes, a Main Street, and hardly a drop of sprawl. An active effort is under way to lure newcomers; the entire Northeast Kingdom region has development programs for small-business entrepreneurs—an important part of the local economy. Make sure you stop at this library and art gallery when you visit St. Johnsbury.
9. Johnson
Johnson, VT 05656, USA
Flickr/boumanm
Johnson Village represents the community’s cultural, commercial, and institutional center. The village is a compact community that is home to a number of unique businesses, heritage buildings, and residential neighborhoods. The village has long been a center for education, and today, approximately 42% of in-town jobs are in educational services. Johnson State College’s roots go back to Johnson Academy School, founded in 1828. Today, Johnson State College has approximately 1,950 students. Read more about why Johnson is worth a stop.
10. Chester
Chester, VT 05143, USA
Flickr/Dougtone
Windsor County’s Chester is one of the best towns in VT, and is best known for its Stone Village and Chester Village Historic Districts. Both of these are listed in the National Register of Historic Places. Learn more about Chester and what you can do and see here.
11. Dorset
Dorset, VT, USA
Flickr/Dougtone
A quiet and charming community, Dorset is nestled in the highest valley between New York City and Montreal. With its charming center and welcoming locals, Dorset has been a summer destination since the early 20th century. See how you can turn a visit to Dorset into a day trip.
12. Grafton
Grafton, VT, USA
Flickr/mksfca
Be sure to visit Grafton if you enjoy historic buildings to get a glimpse into America’s early colonial days. This picturesque village lies in the mountains of southern Vermont, and the residents have restored many of its original buildings to preserve its authentic New England atmosphere. Visitors can enjoy snow-covered hills and cross-country skiing, or wander the town’s array of shops and galleries. The Grafton Inn is a great main street VT location and is the perfect place to sit back with a lemonade and soak in the ambience of this lovely village. Grafton has all you need for a true New England experience.
13. Stowe
Stowe, VT 05672, USA
Flickr/Dougtone
One of the coolest towns in VT, Stowe is an ideal destination in all four seasons, and attracts a large number of visitors for both its outdoor adventures and its charming downtown. In town, visitors can wander arts and crafts studios, museums and galleries, attend musical and theatrical performances, and partake in seasonal activities, such as outdoor block parties and parades. Here are a few more reasons why you've got to stop in Stowe.
14. Weston
Weston, VT 05161, USA
Flickr/djtracitaylor
The small town of Weston, located in Windsor County, offers visitors an authentic, New England country experience. Visit quintessential country stores and shops, where you’ll find everything from Christmas ornaments, crafts and artisanal goods, unique galleries and craft studios (all of which are still family owned and operated). There are also wonderful historical museums and houses to visit as well as theatrical productions. Weston is the perfect place for a quiet change of scenery in a picturesque town with a charming and well-preserved heritage. Check out all that Weston has for visitors.

These are just some of the best downtowns in VT. Vermont has so many more quaint villages! We’d love to know what your favorite main street in VT is!

Now that you’ve picked out some of the coolest towns in VT to check out, what about where to stay? Take a look at these unique places to stay in Vermont.

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best downtowns in VT

Rachel Raimondi | June 18, 2022

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