10 Of The Friendliest Towns In Vermont
One of the oldest cross-country ski races in North America, multiple Winterfests, and town-organized restaurant weeks are just a few of the annual events that make these Vermont towns among the friendliest places in the state. Towns like Stowe, Montpelier, and Rutland connect residents and travelers through world-class ski hills like Stowe Mountain Resort, and culinary and cultural attractions that encourage every visitor to enjoy the local way of life. Together, these Vermont towns are among the most welcoming and friendly to visit in the state.
Stowe
Stowe is one of Vermont’s most visited destinations, located beneath Mount Mansfield, about 35 miles east of Burlington. Stowe Mountain Resort has drawn skiers here since 1937; today it spans roughly 485 skiable acres with 116 trails reaching nearly 4,395 feet. Lift lines, base lodges, and the village at Spruce Peak mix locals, seasonal workers, and destination travelers, creating a friendly atmosphere further enhanced by the town's annual events.
The Stowe Derby, first run in 1945, sends cross-country racers from Mansfield’s Toll Road down to a village finish, where spectators line the Stowe Recreation Path and wait for friends and family to appear out of the trees. During the Stowe Winter Carnival, professional ice carvers shape blocks in full public view on the Village Green before judges award prizes, keeping crowds circulating between demonstrations and the awards ceremony. During the fall, the Stowe Foliage Arts Festival takes over with live music, while the British Invasion Car Show fills Main Street with restored MGs, Jaguars, and Minis.
Brattleboro
At Vermont’s southeastern edge, where the Connecticut River forms the New Hampshire border and the West River meets it downtown, Brattleboro pulls together three neighboring states into a small town of brick storefronts and repurposed industrial buildings. Inside the restored Union Station building, the Brattleboro Museum & Art Center, founded in 1972, rotates exhibitions that draw regional artists, art lovers, and school groups. A few blocks away, the Vermont Jazz Center presents concerts and workshops that mix touring musicians with local players.
Brattleboro's annual events foster an inclusive and charming atmosphere, with October's Brattleboro Literary Festival among the biggest draws and the first Fridays of most months hosting the Gallery Walk. Downtown Brattleboro also puts on the Bratt Luck Crawl in March, which sends participants around town to taste locally made beers, wines, chocolates, cheeses, and so much more.
Woodstock
October crowds gather on the Village Green in Woodstock for the Woodstock Apples & Crafts Fair. During which, juried artisans line the grass with handmade goods and food, turning the center of town into a full-scale public marketplace. The same Green hosts June through October's Market on the Green as well as the summer's Thursday Brown Bag Concert Series, where free lunchtime performances bring together office workers, families, and visitors within sight of the white-steepled First Congregational Church of Woodstock, built in 1807.
This undeniably welcoming atmosphere continues in the wintertime with Wassail Weekend, a multi-day holiday festival featuring a parade through the village, horse-drawn sleigh rides, caroling, and ticketed house tours of historic homes. Whether or not Woodstock is in the midst of hosting an annual festival, there are more connections to be made inside the Woodstock Town Hall, where Pentangle Arts presents live theater, concerts, and film screenings.
Montpelier
Montpelier’s downtown grid crosses the Winooski River, with the Vermont State House (1833) rising above State Street and the river bridges that feed north-south traffic through the city. From June into early October, the Montpelier Capital City Farmers Market populates a parking lot on State Street every Saturday regardless of the weather. In early July, the July 3rd Celebration features an evening of live music and fireworks launched over the restaurant-filled downtown streets. The culinary scene in Montpelier is another reason people flock to the town.
Mid-February's Restaurant Week brings together food lovers of all walks of life to sample a number of the town's eateries, diners, and restaurants like Sarducci's and the Three Penny Taproom. Winter’s events calendar includes WinterFest, a weekend of ice carving demonstrations, performances, and public gatherings, and Ice on Fire, a Sunday‑afternoon sequence of sledding activities, pop‑up storytelling, and a community Christmas tree bonfire.
Rutland
President’s Day week in Rutland means five days of Winterfest, a winter event that turns the city into a network of more than 30 free and low-cost gatherings. Ice sculptures line downtown blocks near Depot Park, fat bikes cut across groomed singletrack, and teams strap into life-size human foosball while a frosted fairytale ball pulls families into the same orbit. Rutland stands in central Vermont between the Taconic Mountains to the west and the Green Mountains to the east, with Killington Peak rising beyond the city line. Killington Resort and Pico Mountain are both outside Rutland’s city limits but within a short drive, which channels skiers and snowboarders back into downtown restaurants and gathering spots after a day on the slopes.
During the holiday season, visitors can enjoy the Downtown Tree Lighting at Depot Park, which brings Santa by fire truck before the tree is illuminated, and the Holiday Window Contest, which encourages tourists and residents to vote on decorated storefronts, turning downtown sidewalks into a full-scale participatory event.
Newport
Newport occupies a pivot point on Lake Memphremagog, the deep lake that threads north into Canada, with the water’s edge and the lake’s border location shaping townspeople’s calendars around the seasons. Waterfront gatherings around Prouty Beach bring anglers and swimmers together in the summer, while each winter the Memphremagog Winter Swimming Festival draws spectators who stand along the shore while cold‑water swimmers complete laps in a 25‑meter, two‑lane ice pool cut into the frozen lake.
February's Fire and Ice snowmobile racing scene on the east side of town pulls riders and fans from multiple states into a clustered venue near Eastside Restaurant. Main Street’s Winter Saturdays series at The Tasting Center appeals to visitors interested in engaging with the town's thriving culinary scene. The series includes local craft tastings and themed evenings.
Manchester
The town of Manchester spreads across the Battenkill River valley with Mount Equinox to the east and the Taconic Range to the west. Hildene, the Lincoln Family Home, sits on 412 acres in the village, with a Georgian Revival mansion, formal gardens, a 12-mile trail system, and Hildene Farm, where visitors watch goat dairying, cheesemaking, and production gardens in action. In the spring, peony season fills the property's gardens with thousands of blooms, while Victorian Christmas illuminates the mansion and welcomes families to take part in old-fashioned Christmas celebrations.
The town really comes together during Memorial Day weekend's Manchester Food & Wine Festival. Multiple venues across town take part in this annual event, letting locals and visitors taste and explore Manchester's culinary scene together. Classical music fills the Arkell Pavilion at the Manchester Music Festival, where seven weeks of performances by rising and established artists connect audiences with musicians in an intimate setting.
Shelburne
Rolling hills and ancient trees frame the village green in Shelburne. Every August, the Shelburne Day Celebration fills this space with games, local food, and music, bringing together hundreds of people each year. Just outside of downtown, the Shelburne Harvest Festival at Shelburne Vineyard offers hayrides, crafts, and agricultural demonstrations that highlight Vermont’s farming heritage. Shelburne Farmers Market draws neighbors and visitors alike from spring through fall.
The Vermont Teddy Bear Factory is one of the town's most beloved attractions. It opens its doors year-round for guided tours of the assembly line, showing each bear being hand-stuffed and sewn, and includes a visit to the Bear Hospital, where broken or worn bears are repaired. Guests can create their own bear in the Bear Shop and watch craftspeople hand-finish every detail, offering an intimate, hands-on experience. Then there's Shelburne Farms, which is spread across 1,400 acres, letting visitors watch cheesemaking, see raptors, wander nature trails, or interact with farm animals, creating hands-on experiences that connect locals and visitors in every season.
Middlebury
Middlebury stretches along Otter Creek, the college lawns and red-brick storefronts brushing up against the water. On warm evenings, the Festival on the Green fills the town green with live music, food from local vendors, and kids running between lawn games, blending students, families, and visitors in one open space. Wednesdays from June through October, the Addison County Farmers Market turns the town green into a rotating stage of produce and crafts, with musicians playing between stalls.
Visitors also find community with residents who share a love of history and culture found at the Henry Sheldon Museum of Vermont History, which hosts exhibits and workshops for all to take part in. Annual events include the Middlebury Maple Run, which invites people from across New England to participate in the half-marathon.
Ludlow
Mount Okemo towers above Ludlow, drawing skiers to its 667 acres and 123 trails, while the mountain's Adventure Zone spins into motion with zipline tours, a mountain coaster, bungee trampolines, climbing walls, and miniature golf. Families and visitors gather here across seasons, shifting from winter slopes to summer adventures. In the village, the Ludlow Rotary Penny Sale, which has run for well over 65 years, turns the elementary school gym into a buzzing hub, awarding over $15,000 in prizes and funneling proceeds into scholarships and local food programs.
Autumn brings the Ludlow Harvest Fair, filling the streets with food trucks, games, and 45 vendors, while the Best of Vermont Summer Festival spreads across multiple venues with music, classic cars, artisan foods, hot air balloons, and antique tractors. Historic buildings like Black River Academy and the old post office line the streets, inviting festival-goers to explore between events.
From the Stowe Derby’s start line on Mount Mansfield to Middlebury’s Festival on the Green along Otter Creek, Vermont’s towns build in opportunities for connection, whether it's through events or intimate attractions. Manchester combines historic sites like Hildene with music festivals that fill village streets, and Ludlow’s Okemo slopes and Adventure Zone generate year-round engagement. In each case, these towns create environments where people meet, participate, and interact naturally, proving that friendliness distinguishes these Vermont communities.
