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8 Most Charming Towns in Vermont

It’s no coincidence that, imagining Vermont, you can almost taste the crisp mountain air while standing in a pretty cityscape with peaks on all sides. With pretty steeples and historic buildings, these cityscapes blend into the great outdoors, like the most charming in Vermont.


Old buildings along Whetstone Broke in Brattleboro, Vermont

Despite an industrious past in textiles, paper, machine mills, and several manufacturers, Brattleboro retains a small-town ethic. Known for a strong liberal counterculture thought that developed between the 1960s and 1970s, the vibe in town is as inimitable as its name. Home to many working artisans, artists, and musicians, Brattleboro attracts like-minded people to visit and see what this special place is all about. The bustling streets full of art are dotted with many small shops, galleries, bookstores, cafes and small ethnic cafes. The main street is full of billboards for upcoming performances, concerts, classes, charities and social events. There’s also the Brattleboro Farmers’ Market on Saturday mornings from May through October, with lunch stalls from five continents where locals and tourists alike gather to eat, people-watch and mingle to the sounds of live music. There, one can stock up on locally grown fresh produce and seek out handicraft souvenirs, fine chocolates, farm-fresh cheese and aromatic bread. Among the town’s festivals, the Heifer Walk is a lovely annual spectacle of children parading local cattle down Main Street.


An aerial view of Chester in the fall

Located in the south of the state, Chester is the perfect base for outdoor adventures, with plenty to offer in its charming cityscape adorned by the Green Mountains. People flee to the city during the holiday season for fun in the snow, including all winter sports, as well as during the warmer months for hiking, biking and mountaineering. In the city full of history, one will find the atmosphere of the historic district of Stone Village dominated by Victorian granite houses and the Chester Factory Village known for its mixture of Federal and Colonial architecture. Listed on the National Register of Historic Places, their New England aesthetic blends charmingly with every inn and antique shop. For contemporary entertainment, there are plenty of art galleries, excellent restaurants and artisan shops to browse and stock up on unique gifts for your loved ones. There are active adventures for all abilities on Mount Snow and Killington, while proximity to Okemo opens up more opportunities for biking, boating and skiing, surrounded by different sites. Chester’s annual Autumn Festival sees huge gatherings and mixing of tourists and locals in September.


Mad Tom Orchard in East Dorset, Vermont

Located in the southern part of the state, tiny Dorset of 200 residents offers a charming experience of authentic small-town Vermont living. A place where locals know each other by name, the town makes visitors feel at home in no time, with plenty of B&Bs everywhere. Dorset is a particularly popular destination for extreme enthusiasts looking to get away from it all in scenic surroundings. They get their adrenaline fix at Dorset’s famous marble quarry for cliff jumping. Of historical significance, the nation’s first-ever marble quarry is located just off Route 30 for easy access to a “cool” spot on a hot summer day. For more relaxation, Emerald Lake State Park is ideal for shaded walks along hiking trails, swimming, canoeing, and kayaking in the lake’s blasé waters. The town is set over hills and valleys, with nearby Dorset Mountain and Bromley Mountain appealing to winter sports fanatics. Dripping with quintessential New England charm, Dorset is also a vibrant arts and culture destination, with marble quarry stone pavements, a marble church next to the village green and the main branch of the New York Public Library. The festival and parade lineup includes the popular and beloved Dorset Theater Festival.


A map of the location of Greensboro

Embraced by New Hampshire to the east and Canada to the north, Greensboro looks like a distant land, affectionately referred to as the Kingdom of the Northeast by a former US senator and now residents. The unique and secluded atmosphere is even more magical on the charming shores of the crystal clear Caspian Lake. Filling the lakeside cottages, the population of less than 1,000 doubles during the summer and has hosted the likes of Margaret Mead for work, as well as Pulitzer Prize winner Wallace Stegner who used it as a setting for his novel. The city’s proud performing arts scene includes the Highland Center for the Arts which presents year-round performances of music, theatre, dance, film workshops and lectures. Exhibitions and events take place in a state-of-the-art 250-seat theater and a smaller performance hall. There is also an art gallery and a summer cafe. At the same time, the Mirror Theater plays host to both professional actors and local talent during the summer, which is also the season for the youth circus arts program at Circus Smirkus, headquartered in Greensboro. In the city, Willy’s store is the gathering place for all, with an original motto, “if we don’t have it, you don’t need it”. While there, the Miller Thumb Gallery across the street, works by artisans and artists from Vermont and New England are on display in an old flour mill. For nature lovers and the active, there’s Greensboro’s highest point, Barr Hill, surrounded by the Barr Hill Nature Preserve, with trails and scenic views up to Mount Mansfield.


Robert Tod Lincoln’s 1905 Georgian Revival Summer Home and Gardens in Manchester, Vermont

Known for its pretty spiers and historic buildings, Manchester is divided into the distinctively charming Manchester Village and Manchester Center. The former is known for its atmospheric walks on marble sidewalks lined with beautifully maintained mansion-like homes. The whole of historic Manchester Village is listed on the National Register with the central masterpiece of the Equinox Hotel. Also worth visiting is the Georgian Revival Hildene overlooking the Battenkill Valley on the edge of Manchester Village, built by Robert Todd Lincoln, son of Abraham Lincoln. Included are beautiful gardens open to the public, a working farm, goat cheese factory and a fantastic Pullman car. There’s also the American Fly Fishing Museum with antique pieces and art, while the Southern Vermont Arts Center is dotted with large sculptures and has temporary exhibits. The Manchester Center is the shopping counterpart where shoppers head to high-end outlet stores for designer clothing brands, kitchenware and everything in between. For panoramic views, active people can climb Mount Equinox via a trail also accessible via the Skyline Drive toll road to see all of the surrounding mountains. Nearby Bromley Mountain is the winter sports destination and home to one of the longest ziplines in the state. There are also some four hundred thousand acres of unspoiled wilderness in the nearby Green Mountain National Forest for hiking, biking, or leisurely strolling and relaxing with a picnic.


The skyline of Montpellier, Vermont

Montpelier, the capital of Vermont and the least populated of its kind in the country, sees many people travel to its charming cityscape for work. Retaining a small-town feel with around 8,000 residents, Montpelier caters to residents and visitors alike with attractions, venues and establishments. The Vermont State House and the Vermont History Museum offer to teach how the city is run and came to be through historical and governmental facts. Picturesque Montpelier’s charm is also evident in a vibrant cultural scene of history, art and music, including the Vermont Historical Society Museum and the TW Wood Art Gallery. Nature lovers will love strolling through Hubbard Park, which is also a great place for people-watching, while the charming farmers’ markets offer more of a mix and a real “taste” of the mountain township. Foodies will enjoy sampling the huge cuisine in lively restaurants and cute cafes, as well as visiting the Montpellier-based New England Culinary Institute.


Lake Champlain and the Adirondack Mountains in Shelburne, Vermont

Located near the state’s largest city, Burlington, beautiful Shelburne is the the best of the best of the megalopolis, where people flee steel and fumes. There is the perfectly appointed Shelburne Museum with a fascinating American art and design collection housing impressionist paintings, American trinkets and a historic steamship, the only one of its kind in the world. Over a dozen historic buildings spread over 45 acres near the museum with over 150,000 additional works. Active tourism enthusiasts will enjoy visiting the Covered Bridge Museum, as well as the huge Lake Champlain, for an excellent retreat with opportunities for recreation in nature. Known for its width of 514 square miles, the lake is bordered by Quebec on the other side and offers divine sunsets, all water sports, sailing and swimming in the glassy waters. Back in town, one will find healthy shopping and dining options to suit all tastes. Proximity Shelburne Farms offer a scenic farm environment for families, animals and educational programs for the little ones.


The village of Stowe in Vermont in the fall

Located in the northern part of the state, Stowe is an incredibly scenic and charming town nestled beneath Vermont’s tallest mountain peak, Mount Mansfield. A popular destination for climbers and hikers, there is also Smuggler’s Notch State Park, which is an outdoor enthusiast’s dream for skiing and snowboarding in winter, camping, hiking and biking during the summer months. Winding through trails and a mountain pass, there are many scenic hidden waterfalls waiting to be discovered, including Bingham Falls and Moss Glen, known for picnics, base swimming and photo ops. The town is a favorite among art junkies, as the famous location where the von Trapp family of The sound of music moved after fleeing Austria during the Nazi era. One can visit the Trapp Family Lodge telling their rich history through exhibits, artifacts and stories. For more pieces unique to the culture of this region, visit the Vermont Ski and Snowboard Museum.

These towns will delight anyone who loves the mountainous environment and appreciates the charming way small towns welcome tourists. One will leave with lasting memories of atmospheric strolls through the pretty streets feeling the benevolent embrace of the mountains from their awe-inspiring position.