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12 Most Charming Towns in Vermont

Vermont may be one of the smallest states, but it has lots to offer. With many lakes, streams, soaring mountains, and over three-quarters of it covered in forest, it’s an outdoor adventurer’s paradise. There are also some very charming towns with friendly people, farm-to-table eateries, and all sorts of local items, from maple syrup to fresh produce, that make Vermont’s charming towns the perfect base for enjoying all there is to do and see.

Bristol Bristol, Vermont
Credit: Bristol, Vermont by © Linnaea Mallette | Dreamstime.com


Located in the Green Mountain foothills, Bristol’s downtown is a National Historic District with flat-roofed buildings lining the wide main street. It looks a bit like an old western town with a New England twist. While there are plenty of modern amenities like breweries, restaurants, and art galleries, there’s a big focus on history, with the recycling even picked up by a horse-drawn wagon. Beyond that, this is a place of festivals, with many events to enjoy, including the Pocock Rocks Street Fair in June and the Bristol Band summer concerts that have been held here since the end of the Civil War. Visitors come from far and wide to be here for the Great Bristol Outhouse Race, the longest-running of its kind in the country, hosted as part of the Fourth of July festivities.

Weston Weston, Vermont
Credit: Weston, Vermont by bigstockphoto.com


Weston is one of those towns that looks like it stepped out of a Norman Rockwell painting, with the entire village a historical landmark. The streets are lined with impressive New England-style homes, family-owned country stores, and cozy B&Bs. There are several museums to visit as well, including the Old Mill Museum, which hosts an excellent collection of antique tools and provides milling demonstrations. Get a glimpse of the 19th-century Industrial Revolution at the Vermont Scale Museum which features antique Vermont Scales, or explore a Vermont Homestead at the Farrar-Mansur House Museum.

Woodstock Woodstock, Vermont
Credit: Woodstock, Vermont by © Sean Pavone | Dreamstime.com


Woodstock is often named among the country’s most beautiful towns. Located along the banks of the Ottauquechee River, it’s quintessential New England, complete with a picturesque covered bridge, country farms, pretty parks, and magnificent homes built in Georgian, Federal, and Greek Revival styles. Just wandering through is enjoyable, with the feel as if you’re stepping into a postcard from another time. There’s plenty to do, including visits to the Billings Farm and Museum to learn about New England life in the 19th Century and Marsh-Billings-Rockefeller National Historical Park, with over 20 miles of scenic trails to hike. Whatever you do, don’t miss sampling the maple syrup and cheese at Sugarbush Farm.

Chester Chester, Vermont
Credit: Chester, Vermont by © Steve Callahan | Dreamstime.com


Located in southeast Vermont, where three branches of the Williams River meet, and surrounded by the peaks of the Green Mountains and rolling farmland, Chester offers plenty to entice in one of Vermont’s best places to visit. The downtown historic district hosts beautifully maintained homes, some dating all the way back to the mid-1700s. It’s an enjoyable spot to stroll with plenty of fun shops, bookstores, vintage barns selling country-style items, and more than 90 antique dealers at The Stone House Antique Center. There’s another historic district, too; the Stone Village Historic District includes ten magnificent Greek Revival buildings made of stone from local quarries that were designed and built by Scottish settlers. There’s even a Scottish pub to enjoy after exploring.

Waitsfield Waitsfield, Vermont
Credit: Waitsfield, Vermont by © Joe Sohm | Dreamstime.com


Located near the capital city of Montpelier in the Mad River Valley and perfect for a Vermont weekend getaway, Waitsfield is a free-spirited place with a true sense of community. It attracts many creative types, like musicians, potters, chefs, and artists, and there’s also a wide range of delicious and often farm-fresh organic eats. Straddling the banks of the Mad River, scenic views are easy to find, and there are plenty of fun outdoor activities year-round, including hiking and snowshoeing. Don’t miss a visit to Hartshorn Organic Farm, which offers farm tours and frequently hosts workshops and food festivals. By visiting its maple sugar house, you can learn all about the maple syrup-making process too.

Manchester Robert Todd Lincoln’s Ancestral Home in Manchester, Vermont
Credit: Robert Todd Lincoln’s Ancestral Home in Manchester, Vermont by © Lei Xu | Dreamstime.com


Manchester is a popular escape among city dwellers seeking tranquility and as a top summer family vacation destination in Vermont, as there are just so many things to do. Shoppers can shop ’til they drop at the factory outlets and check out the vibrant cultural scene with museums, galleries, theaters, and concert venues. There’s also lots of history to discover, including Robert Todd Lincoln’s Ancestral Home, a 1905 Georgian Revival summer home with a formal garden. The historic estate was the home of the only Lincoln child who survived to adulthood. Fly fishing enthusiasts are catered to as well at the unique American Museum of Fly Fishing, which showcases rods, flies, and angling-related art. When it’s time to dine, you’ll find various restaurants and cafes serving tasty artisanal fare as well.

Brattleboro Brattleboro, Vermont
Credit: Brattleboro, Vermont by © Jon Bilous | Dreamstime.com


One of New England’s most picturesque towns, Brattleboro offers a fabulous downtown area with indie bookstores, art galleries, museums, unique shops, outstanding eateries, and a great farmer’s market. It’s also home to a covered wooden bridge that’s the only surviving example of its kind in the region. Many outdoor activities can be enjoyed, including kayaking, canoeing, hiking, and biking during the warmer months, while winter brings opportunities for ice fishing, cross-country skiing, and snowshoeing. A number of fun annual events are hosted as well, including a brewers’ festival, a literary festival, and the Independence Day parade.

Dorset Dorset, Vermont
Credit: Dorset, Vermont by © Jennifer Lobo | Dreamstime.com


The historic community of Dorset was founded in 1761. Nestled in the hills of Bennington County in southern Vermont, its streets are lined with clapboard homes while lush greenery is strewn throughout. Home to the country’s oldest marble quarry, it’s popular for swimming during the warmer months. At the Bley House Museum, you can learn more about it in the Marble Gallery. The Dorset Theatre Festival, hosted throughout the summer in a theater built from pre-revolutionary barns, is worth planning a trip around, while the farmer’s market is always a delight with its many fresh fruits and vegetables, artisan cheeses, home-baked bread, grass-fed meats, Vermont crafts and much more.

Stowe Stowe, Vermont
Credit: Stowe, Vermont by © Arthur Caiado | Dreamstime.com


Another postcard-perfect town often on lists of the most picturesque is Stowe. Located in the northern region next to Mount Mansfield, the state’s highest peak, it’s especially popular among nature lovers and adventurers. Home to Smuggler’s Notch State Park, it’s a great place to hike, bike, and go cave exploring during the warmer months and ski or snowboard in the wintertime at Stowe Mountain Resort, one of Vermont’s top ski resorts. In the charming village itself, there are covered bridges and church steeples with a spectacular backdrop of the Green Mountains. You’ll find lots of fabulous made-in-Vermont items like maple syrup and cider donuts, too.

Wilmington Wilmington, Vermont
Credit: Wilmington, Vermont by © Bdingman | Dreamstime.com


The village of Wilmington is aesthetically pleasing, nestled at the southern end of the Green Mountains. The historic downtown area offers a great way to spend the day with many fabulous local eateries serving the best of the bounty of the land. There are many independent boutiques, antique shops, specialty stores, and bookshops to browse. If you visit on the weekend, a flea market is hosted with local vendors selling handcrafted items, souvenirs, local food, and more. Just outside of town, there are a number of scenic hiking trails, including Hoot, Toot, and the Whistle Trail, the Valley Trail, and the Hogback Mountain trails.

Waterbury The Ben & Jerry's Factory in Waterbury, VT
Credit: The Ben & Jerry's Factory in Waterbury, VT by benjerry.com


Tucked into the Green Mountains in the center of the state, Waterbury is home to quaint country stores offering local produce and other goods, as well as the Cold Hollow Cider Mill, which sells maple syrup, cider donuts, and Vermont Cheddar. It’s one of the best bike towns in the state, with an acclaimed network of trails, while Camel’s Hump State Park is ideal for hiking enthusiasts. Of course, many people know it as the home of Ben & Jerry’s, attracting those who want to take a factory tour and enjoy some of the best ice cream. Beer lovers will find a surprisingly impressive craft brew scene as well.

Middlebury Middlebury, Vermont
Credit: Middlebury, Vermont by © Jim Lawrence | Dreamstime.com


Tucked between the Champlain Valley and the foothills of the Green Mountains in western Vermont, Middlebury offers lots of charms with a picturesque downtown area, a classic white steepled church, lovely parks, and even a ski area right within the town limits. During the warmer months, rent a bike and ride the 16-mile loop that wraps around the town or hit the trails in the 400,000-acre Green Mountain National Forest, one of Vermont’s most beautiful parks. The Robert Frost Interpretive Trail is a short but sweet one-mile loop peppered with quotes from Frost’s work. In season, blueberry picking is possible at one of the many farms in the surrounding area. There are plenty of venues for shopping and dining, and you’ll find a theater too.

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