View of the historic and colorful Manchester Village in Manchester, Vermont with tulips in bloom

The Most Picturesque Small Towns in Vermont

Vermont, a sparsely populated landlocked US State forms a part of the American Northeast’s New England region, wedged between the Canadian province of Quebec, and the neighboring states of Massachusetts, New Hampshire, and New York. Flaunting comprehensive sights of flourishing green rolling hills during the warm summers, the transcendent yellow-red shades in fall, the snowy-white landscapes in winter, and the wildflower-covered fields in spring, the state never falls short of mesmerizing vacationers regardless of their time of visit. Even though the state capital, Montpelier, and the most populous city, Burlington, are at the top of the lists of a majority of tourists, the innumerable small towns dotting Vermont’s 9,250 sq. mi. terrain are equally worth touring for an unforgettable holiday in the Green Mountain State.


Downtown Grafton, Vermont.
Downtown Grafton, Vermont. Image credit Doug Kerr, CC BY-SA 2.0, via Wikimedia Commons

Originally a widely-known soapstone mining center by the side of the Saxtons River and a prominent stagecoach mecca for vehicles crossing the Green Mountains, Grafton is a teen picturesque town in southern Vermont’s Windham County. The glorious bygone days of this 645 inhabitants’ community is well displayed in the numerous landmark properties such as the Grafton Inn, which the Windham Foundation has meticulously restored besides several of the town’s residences. Travelers visiting Grafton must not miss the plethora of small businesses like Plummer’s Sugar House, Phelps Barn Pub, Grafton Village Cheese Company, Rushton Farm, MKT: Grafton, and many more. For adventure seekers, the Grafton Trails & Outdoor Center provides mountain biking, hiking, and swimming activities during summers and snow tubing, snowshoeing, sleigh rides, skiing, and fat biking in the winter months.


Ticonderoga steamboat, Shelburne, Vermont
Ticonderoga steamboat, Shelburne, Vermont. Image credit Wangkun Jia via Shutterstock

An enchanting settlement on the shores of Lake Champlain in Chittenden County, the heart of the town is situated exactly 7 miles south of the urban core of Burlington. Vacationers touring Shelburne delight in the incredible Green Mountain vistas, the luxuriant valleys, and the abutting painstakingly maintained farms. The panoramic Lake Champlain is excellent for water-based recreation such as fishing, swimming, boating, kayaking, canoeing, or simply unwinding at the immaculate lakeside beach. Furthermore, the Shelburne Museum, Shelburne Orchards, Shelburne County Store, Vermont Teddy Bear Company, Shelburne Vineyards, and Shelburne Farms are must-visit sites of interest. All year round, merrymakers can partake in various events like the Shelburne Day celebration, a summer concert series by Shelburne Farms, and the Shelburne Farmers Market.


Spectacular Stowe, Vermont, in the fall.
Spectacular Stowe, Vermont, in the fall.

Stowe, dubbed “The Ski Capital of the East,” occupies an extensive verdant valley in Lamoille County bounded by the Worcester Range to the east and Mount Mansfield - the state’s highest peak and other Green Mountain peaks to the west. Chartered in 1763 by Benning Wentworth - the Royal Governor of the Province of New Hampshire, Stowe is an outstanding four-season holiday getaway providing superb skiing and snowboarding facilities at Stowe Mountain Resort and world-class cross-country ski trails at Stowe Nordic. During fall, the vivid colors of the encircling tree-covered mountains make Stowe ideal for mind-blowing photo shoots aside from supplementary outdoor recreational activities such as hiking, mountain biking, and horse riding. Walk down the alluring Main Street and peruse the umpteen special shops and upscale eateries like Harrison’s Restaurant and The Bistro at Ten Acres. Additionally, tour the epochal white-steepled Stowe Community Church, the Stowe Visitor Center, the Gold Brook Covered Bridge, the Trapp Family Lodge, Stowe Recreation Path, Smugglers’ Notch State Park & Recreation Area, and Spruce Peak Performing Arts Center.


The old covered bridge in Woodstock, Vermont.
The old covered bridge in Woodstock, Vermont.

This shire town of Windsor County is located next to the Ottauquechee River’s south branch, roughly 250 miles from New York City and a three-hour drive away from Boston. Colloquially called the “Green,” the idyllic central square of Woodstock is abutted by a large number of conscientiously renovated structures in varied architectural styles. The Billings Farm & Museum, Marsh-Billings-Rockefeller National Historical Park, Windsor County Courthouse, Norman Williams Public Library, the timber-framed Taftsville Covered Bridge, Woodstock History Center, and F. H. Gillingham & Sons are some noteworthy attractions. Every year, Woodstock hosts the Bookstock Literary Festival, Harvest Weekend at the Billings Farm & Museum, and Wassail Weekend in June, October, and early December respectively.


Historic Vermont County Store in autumn in Weston, VT
Historic Vermont County Store in autumn in Weston, VT. Image credit Photos BrianScantlebury via Shutterstock.

Encircled by the lush Green Mountain National Forest, Weston provides tranquil settings for approximately 623 inhabitants as per the latest US Census. This Windsor County community is held in high esteem for its spellbinding amalgamation of ancient heritage and impressive natural surroundings. Countless untarnished 19th-century properties including the Weston Playhouse, the Farrar-Mansur House, and the Old Mill fill the National Register-listed Weston Village Historic District. Instituted in 1935, the Weston Playhouse Theatre Company is Vermont’s longest-running professional theatre that presents an array of performances all around the year. The peaceful Weston Priory, the traditional goods-selling Vermont Country Store, and Weston Village Green - a venue for a variety of amusement events are some notable places of interest.


Aerial view of Waitsfield, Vermont.
Aerial view of Waitsfield, Vermont.

Waitsfield, christened after General Benjamin Wait, sits at the nucleus of Mad River Valley along Vermont Route 100, betwixt Northfield Mountains and the Green Mountains’ principal range in Washington County. The Mad River Valley region not only entices thousands of holidaymakers for its breathtaking scenery but also for the stupefying Mad River Glen Ski Area, whose terrain is believed to be the toughest on the East Coast. In addition to the Mad River Glen Ski Area, the adjoining Sugarbush Resort also provides crucial support to Waitsfield’s economy. The other unique points of interest include the Artisans’ Gallery, Madsonian Museum of Industrial Design, Mad River Glass Gallery, Skinner Barn, Big Picture Theater & Café, Lawson’s Finest Liquids Brewery, Hartshorn Organic Farm & Maple Sugar House, Mad River Path, and the Round Barn Farm.


Main Street, scenic Brattleboro, Vermont, looking north
Main Street, scenic Brattleboro, Vermont, looking north, via Bob Korn /

Called Brattleborough at the outset, this adorable tiny Windham County community is set at the junction of the West and Connecticut Rivers in the Connecticut River Valley, around 10 miles north of the Vermont-Massachusetts state boundary. As one of the favored commercial and tourist retreats of the state, Brattleboro aptly amalgams a rustic atmosphere with modern-day conveniences. The lively downtown is chock-a-full of retail stores, farm-to-table restaurants, coffee shops, entertainment spaces, bookstores, and art galleries. Also being “America’s Best Small Art Towns,” Brattleboro has a thriving arts scene and is home to multiple art organizations like the Brattleboro Museum & Art Center, New England Youth Theater, Hooker-Dunham Theater & Gallery, Windham Art Gallery, etc. The Gibson-Aiken Center is managed by the town in addition to the many parks and outdoor recreation hubs. When in town, find time to attend any of Brattleboro’s yearly festivals such as the Maple Open House Weekend, Brattleboro Women’s Film Festival, Winter Carnival, Brattleboro Literary Festival, and Brattleboro Free Folk Festival.


Colorful restaurant in Manchester, Vermont.
Colorful restaurant in Manchester, Vermont.

Manchester, one of the said two seats of government of Bennington County, is located near the Batten Kill River fringed by the Taconic Range to the west and the Green Mountains to the east. An exemplary all-season holiday destination, this former iron-mining town tempts holidayers with its emblematic white steeple churches, popular restaurants, home-like accommodations, art galleries, antique shops, locally-owned breweries, and ancient structures like the Bennington County Courthouse and Hildene - The Lincoln Family Home. At the time of summer and spring seasons, hikers prefer to traverse the Prospect Rock trail or tour the Merck Forest & Farmland Center; while in winter, the nearby downhill slopes of Stratton and Bromley Mountains are ideal for skiing. Stop by the Southern Vermont Arts Center and take note of the exhibits, visit the Northshire bookstore, and explore the North Meadow Farm, Dana L. Thompson Memorial Park, American Museum of Fly Fishing, Equinox Preservation Trust, Lye Brook Falls, and Earth Sky Time Community Farm.

From the paradisiacal agrarian town of Grafton to the lakeside grandeur of Shelburne, each of the teeny communities exudes a distinctive allure drawing sightseers from worldwide to the 6th smallest and the 2nd least-populous state of the nation. Whether you want to visit the Green Mountain State either for your short weekend getaways or extended vacations, look no further than these postcard-pretty towns boasting stunningly beautiful natural wonders, historic downtowns, ample outdoor recreations in world-class resorts, colorful annual festivities, and eateries serving delectable farm-to-table cuisines.

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