8 Most Charming Towns In Vermont

It is not a coincidence that when picturing Vermont, one can almost taste the fresh mountain air while placing themselves in a cute townscape with peaks to all sides. Having pretty steeples and historic buildings, these townscapes blend in with the great outdoors, as the most charming in Vermont.


Old Buildings Along Whetstone Broke in Brattleboro, Vermont

Despite an industrious past in textile, paper, machinery mills, and several manufacturers, Brattleboro retains a small-town ethic. Known for a solid liberal counter-culture thinking that developed between the 1960s-70s, the vibe in town is as un-replicable as its name. Home to many working craftspeople, artists, and musicians, Brattleboro attracts the like-minded to visit and see what the special place is all about. The vibrantly-decorated streets full of art are strewn with many small shops, galleries, book stores, coffee houses, and little ethnic cafes. The Main Street brims with bulletin boards of upcoming performances, concerts, classes, charities, and social events. There's also the Brattleboro Farmers' Market on Saturday mornings from May through October, featuring lunch stands from five continents where locals and tourists gather to eat, people-watch, and mingle to the sounds of live music. There, one can stock up on fresh, locally-grown produce and browse for souvenirs from the handmade craft, fine chocolates, fresh farm cheese, and aromatic bread. Among the festivals in town, the Strolling of the Heifers is a cute annual spectacle of kids parading local livestock down Main Street.


An Aerial View of Chester During Fall

Set south in the state, Chester is the ideal base for outdoor adventures, with much to offer within its charming townscape adorned by the Green Mountains. People flee to the town around the holiday season for fun in the snow, including all the winter sports, as well as in the warmer months to hike, bike, and mountain climb. In the town full of history, one will find the atmospheric Stone Village Historic District dominated by granite Victorian houses and the Chester Factory Village known for the federal and colonial blend of architecture. Listed on the National Register of Historic Places, their New England aesthetic charmingly blends between all the inns and antique shops. For contemporary entertainment, there are many art galleries, great restaurants, and artisan shops to peruse and stock up on unique gifts for your loved ones. There are active adventures for all levels on Mount Snow and Killington, while the proximate Okemo opens more opportunities for cycling, boating, and skiing, surrounded by different sights. The annual Chester Fall Festival sees huge gatherings and mingling of tourists and locals in September.


Mad Tom Orchard in East Dorset, Vermont

Set in the southern part of the state, the tiny Dorset with 200 residents offers a charming experience of authentic small-town Vermont life. A place where locals know each other by name, the town caters to make visitors feel at home in no time, with many B&Bs throughout. Dorset is an especially popular destination for the extreme-seekers looking to escape into a quaint environment. They find their fill of adrenaline in the well-known Dorset Marble Quarry for cliff-jumping. Historically significant, the first-ever marble quarry in the country is set right off Route 30 for easy access to a "cool" place on a hot summer's day. For more chill-time, the Emerald Lake State Park is great for shaded strolls along the hiking trails, swimming, canoeing, and kayaking the jaded waters of the lake. The town is set on rolling hills and valleys, with Dorset Mountain and the nearby Bromley Mountain calling to the winter sports fanatics. Dripping with quintessential New England charm, Dorset is also a vibrant destination for arts and culture, with stone sidewalks from the marble quarry, a marble church next to the green village, and the main branch of the New York Public Library. The line-up of festivals and parades includes the popular Dorset Theatre Festival beloved.


A Map of the Location of Greensboro

Embraced by New Hampshire to the east and Canada to the north, Greensboro feels like a faraway land, lovingly called the Northeast Kingdom by a former US senator and now the residents. The unique and remote atmosphere is even more magical on the charming shores of the crystal-clear Caspian Lake. Filling the lakeside cottages, the population of fewer than 1,000 doubles during summer and has catered to the likes of Margaret Mead for work, as well as the Pulitzer-Prize winner Wallace Stegner who used it as a setting for his novel. The town's pride-worthy performing arts scene comes with the Highland Center for the Arts presenting year-round performances of music, theater, dance, cinema workshops, and lectures. Exhibitions and events occur in a 250-seater state-of-the-art theater and a smaller performance venue. There's also an art gallery and a summer café. At the same time, the Mirror Theater hosts both professional actors and local talent during summer, which is also the season for the youth circus arts program at Circus Smirkus, headquartered in Greensboro. In town, Willey's Store is the gathering place for all, featuring a quirky motto, "if we don't have it, you don't need it." While there, the Miller's Thumb Gallery across the street showcases works by Vermont and New England craftspeople and artists in a former grist mill setting. For nature lovers and the active, there's Greensboro's highest point, Barr Hill, surrounded by the Barr Hill Nature Preserve, with trails and panoramic vistas all the way to Mt. Mansfield.


Robert Tod Lincoln's 1905 Georgian Revival Summer House and Gardens in Manchester, Vermont

Known for its pretty steeples and historic buildings, Manchester is split into distinctively charming Manchester Village and Manchester Center. The former is known for atmospheric strolls via the marble sidewalks lined by beautifully-maintained mansion-like homes. The whole Manchester Village Historic District is on the National Register with the focally-set masterpiece of the Equinox hotel. One must also check out the Georgian Revival Hildene overlooking the Battenkill Valley at the edge of Manchester Village, built by Robert Todd Lincoln, son of Abraham Lincoln. Inclusive are beautiful gardens open to the public, a working farm, a goat cheese dairy, and a fantastic Pullman car. There's also the American Museum of Fly Fishing with antique pieces and art, while the Southern Vermont Arts Center comes studded with large sculptures and houses changing exhibits. The Manchester Center is the commercial counterpart where shoppers head to the high-end factory outlets for designer clothing brands, kitchenware, and everything in between. For panoramic views, the active can climb Mount Equinox by a trail that is also accessible via the Skyline Drive toll road to see all of the surrounding mountains. The nearby Bromley Mountain is the destination for winter sports and home to one of the longest zip-lines in the state. There are also some-four hundred thousand acres of unspoiled wilderness in the nearby Green Mountain National Forest to hike, bike, or leisurely stroll and relax with a picnic.


The Skyline of Montpelier, Vermont

Vermont's capital and the least-populated of its kind in the nation, Montpelier, sees many people commuting to its charming townscape for work. Retaining a small-town feel with about 8,000 residents, Montpelier keeps busy catering to residents and visitors alike with attractions, venues, and establishments. The Vermont State House and the Vermont History Museum offer to teach how the town is run and came to be through historical and governmental facts. The charming character of the quaint Montpelier also comes through in a vibrant cultural scene of more history, art, and music, including the Vermont Historical Society Museum and the TW Wood Art Gallery. Nature lovers will love wandering through Hubbard Park, which is also a great place to people-watch, while the charming farmers' markets offer more mingling and a real "taste" of the mountainous township. The foodies will enjoy taste-testing the immense cuisine at the lively restaurants and cute cafes, as well as visiting the New England Culinary Institute based in Montpelier.


Lake Champlain and the Adirondack Mountains in Shelburne, Vermont

Set close to the state's largest city, Burlington, the beautiful Shelburne is the crème de la crème of the megalopolis, where people flee from the steel and fumes. There's the perfectly-landscaped Shelburne Museum with a fascinating Americana collection of art and design housing impressionist paintings, Americana curios, and a historic steamboat, the only one of its kind in the world. More than a dozen historic buildings spread over 45 acres near the museum featuring over 150,000 more works. The active sight-seekers will enjoy visiting the Covered Bridge Museum, as well as the immense Lake Champlain, for a great retreat with recreational opportunities in nature. Known for its 514 square mile breadth, the lake is bordered by Quebec on the other side and comes with divine sunsets, all watersports, yachting, and swimming in the glassy waters. Back in town, one will find wholesome shopping and dining choices to suit all tastes. The nearby Shelburne Farms offer a quaint farm environment for families, animals and educational programs for the little ones.


The Village of Stowe in Vermont During Fall

Set in the northern part of the state, Stowe is an incredibly picturesque and charming town nestled under the highest mountain peak in Vermont, Mount Mansfield. A popular destination for climbers and hikers, there's also the Smuggler's Notch State Park, which is a dream for all outdoor lovers to ski and snowboard in the winter, camp, hike, and bike during the summer months. Snaked by trails and a mountain pass, many scenic hidden waterfalls are waiting to be discovered, including the Bingham Falls and Moss Glen Falls, known for great picnicking, swimming in the base, and photo shoots. The town is a favorite among art junkies, as the famous place where the von Trapp family from The Sound of Music moved to after escaping Austria during the Nazi era. One can visit the Trapp Family Lodge telling their rich history through displays, artifacts, and narratives. For more pieces of unique to this region's culture, one must visit the Vermont Ski and Snowboard Museum.

These towns will charm socks off anyone who loves the mountainous environment and appreciates the charming ways small towns cater to tourists. One will leave with lasting memories of atmospheric strolls down the lovely streets feeling the caring embrace of the mountains from their grand stance.