Throughout the year, towns across Windham County come alive with celebrations that showcase everything from our agricultural roots to our thriving arts scene. Here’s some of our favorite annual events, festivals, and fairs that make our corner of Vermont so vibrant in every season.

Winter Wonders

Northern Roots Traditional Music Festival (January)

Baby, it’s cold outside—but the music inside is warming souls! Since 2007, this cozy festival has brought together the diverse musical traditions that shape our region’s unique sound. From foot-stomping Irish jigs to haunting Scandinavian fiddle tunes, you’ll hear the musical DNA of Vermont’s heritage in one welcoming weekend. It’s like a musical family reunion where everyone’s invited, even in the depths of winter.

Bratt Luv Crawl (February)

Just when winter feels endless, downtown Brattleboro transforms into a pre-Valentine’s playground of local delights. Picture this: strolling from shop to shop, being greeted with samples from Vermont’s finest distilleries, breweries, chocolatiers, and cheesemakers. It’s matchmaking magic between our beloved downtown retailers and local artisan food producers—and you get to reap the delicious benefits!

Harris Hill Ski Jump (President’s Day Weekend)

There’s nothing quite like standing at the bottom of this historic 90-meter jump and watching athletes literally fly through the air at 60 mph. Since 1922, this world-class event has put Brattleboro on the international ski map. Bundle up and join hundreds of spectators around bonfires with local food and craft beer in hand. When you hear the crowd’s collective gasp as jumpers soar 300 feet through the crisp Vermont air, you’ll understand why this event has endured for a century.

Spring Awakenings

Vermont Craft Beer & Chili Stroll (March)

As winter loosens its grip, Wilmington invites you to spice things up! This beloved annual event turns the downtown into a savory treasure hunt with local restaurants and home cooks offering their best chili creations alongside craft beer pairings. Between tastings, you’ll enjoy live music and the friendly competition as everyone votes for their favorite heat-bringer. It’s the perfect way to shake off winter and reconnect with neighbors.

Brattleboro Brewers Festival (Memorial Day Weekend)

Kicking off summer proper, this one-day celebration brings together brewers from across the four-state region. What makes this festival special is the chance to chat directly with the passionate people behind your favorite pours. Veterans and newcomers to the craft beer scene mingle easily, with brewers eager to share both their flagship favorites and experimental small-batch creations.

Summer Celebrations

Brattleboro Goes Fourth (July 4)

Independence Day, Brattleboro-style! Our parade has all the small-town charm you’d expect, but with quirky local flair. The highlight for many is the annual reveal of local legend Alfred Hughes Jr.’s top-secret patriotic ensemble—it’s become something of a regional fashion moment! The day flows through music, community games, and culminates with a spectacular fireworks display over the Connecticut River.

Vermont Blueberry Festival (July/August)

For ten delicious days, the historic villages of Wilmington, Dover, Jacksonville, Whitingham, Marlboro, and Readsboro celebrate those tiny blue powerhouses. From picking in sun-warmed fields to themed events like blueberry pancake breakfasts and pie-eating contests, this festival showcases southern Vermont’s sweetest summer crop across multiple communities. The opening parade in Wilmington sets a festive tone for adventures across the region.

Guilford Fair (August/September)

For generations, Guilford’s traditional agricultural fair has marked summer’s transition to fall. It’s where farming traditions are proudly displayed through horse pulls, cattle shows, and sheep shearing demonstrations. The exhibition hall showcases the best homegrown produce and handcrafted items from local gardens and workshops. There’s something profoundly Vermont about savoring maple cotton candy while watching a draft horse competition as summer’s final golden light streams across the fairgrounds.

Fall Favorites

Vermont Wine & Harvest Festival (September)

When the hills begin their spectacular color transformation, the Deerfield Valley hosts this sophisticated celebration of Vermont craftsmanship. Over three days, you’ll sample wines from our hardy northern vineyards alongside cheeses, chocolates, and specialty foods that showcase Vermont’s agricultural innovation. Demonstrations, farm-to-table dinners, and artisan marketplaces spread across the valley, making this a moveable feast against autumn’s dramatic backdrop.

Brattleboro Literary Festival (October)

Book lovers, this one’s our Super Bowl! For four days, downtown Brattleboro hums with literary energy as acclaimed authors and emerging voices gather for readings, panels, and spirited discussions. Since hosting Nobel laureate Saul Bellow in 2002, the festival has welcomed hundreds of distinguished writers while maintaining an accessible, community feel. You might find yourself discussing craft with a Pulitzer winner over coffee at a local café—it’s that kind of magical literary immersion.

Newfane Heritage Festival (October)

For over half a century, the picturesque village of Newfane has transformed its historic common into a celebration of New England craftsmanship during peak foliage season. The crisp scent of homemade apple pies mingles with the visual feast of autumn leaves as thousands browse juried crafts and artwork. This volunteer-run event embodies small-town Vermont at its finest—authentic, welcoming, and set against a postcard-perfect backdrop.

Townshend Pumpkin Festival (October)

When autumn’s colors are at their peak, the Townshend Common transforms into a celebration of all things pumpkin! This cherished community tradition brings together families from across the region for a day of seasonal joy. Children’s faces light up during pumpkin decorating contests and pony rides, while adults enjoy friendly competition in scarecrow-making and cornhole tournaments. As afternoon turns to evening, local musicians provide a soundtrack to your countryside autumn adventure. Between browsing handcrafted goods from local artisans and sampling regional fall harvest treats from food vendors, you’ll experience the authentic charm that makes small-town Vermont festivals so special.

Heirloom Apple Day (October)

At the historic Scott Farm, this free festival celebrates the forgotten flavors of America’s apple heritage. Did you know there are thousands of apple varieties beyond the handful found in supermarkets? Here, you can taste the difference between a tangy Esopus Spitzenburg (Thomas Jefferson’s favorite) and a sweet Cox’s Orange Pippin. Between orchard tours, apple tastings, and cider pressing demonstrations, you’ll gain a whole new appreciation for this iconic fruit in the very landscape where some of these varieties have grown for centuries.

Holiday Happenings

Putney Craft Tour (November)

After Thanksgiving dinner, while others might be shopping mall-bound, southern Vermonters have a different tradition. We follow a self-guided tour through the studios of Putney’s remarkable artisan community. Meeting potters, glassblowers, weavers, and woodworkers in their creative spaces offers insight into their craft that no gallery can provide. The tour extends into evenings with performances at Next Stage and Sandglass Theater, creating a perfect post-holiday cultural immersion.

Jingle Bell Jog (December)

One of The Chamber’s signature annual events, the Jingle Bell Jog brings our community together for this festive 5K through downtown Brattleboro. Runners and walkers don holiday costumes and jingling bells, creating a moving celebration through Main Street. It’s as much about the joy of community as competition—though the serious runners do appreciate the professional timing! Nothing beats the sound of hundreds of jingling bells against the backdrop of a snow-dusted Main Street to put you in the holiday spirit.

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There are so many great events happening in our region all the time—these favorites just scratch the surface! Visit our community calendar to find out what’s happening in Vermont this week, whether you’re planning a visit or looking to explore more of what makes our corner of the Green Mountain State so special.