September in Vermont: 20 Festivals to Kick off Fall in 2026
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Have you noticed that the days are getting shorter? Do you feel that cool fall breeze?
September in Vermont is magical — the leaves are just starting to change, the days are warm, and the nights are cool.
It’s time to throw on a sweater, pick up a maple latte, and explore some fantastic Vermont events.
Vermonters are celebrating the cusp of fall in September.
The foliage season isn’t quite here, so you won’t be competing with throngs of tourists for hotel rooms and restaurant reservations. You will, however, get to experience an abundant supply of apples and farm-fresh veggies, several old-fashioned harvest festivals and fairs, and the friendly hospitality Vermont is known for.
Here are the best events, fairs, and festivals to experience in September in Vermont.
Read this post: The Best Places to Visit in Vermont in the Fall
Vermont Events: September 1-6, 2026
Champlain Valley Fair, Essex Junction, Vermont, August 28- September 6, 2026: The Champlain Valley Fair has been a Vermont institution for the past 104 years! This spectacular Vermont event lasts for a full ten days, with too many special events to list.
This year’s grandstand includes Brantley Gilbert, Gabriel Fluffy Iglesias, and Dustin Lynch, as well as a freestyle motocross show, a huge demolition derby, and a monster truck show.
You’ll also witness traditional farm animals, acrobatic dogs, racing pigs, and sand castle sculptures. Come experience a bit of country life — ride the rides, eat the funnel cake, and enjoy the over-the-top fun at Vermont’s most beloved fair!
Plymouth Folk and Blues Festival, Plymouth, Vermont, September 5 & 6, 2026: Stars from Vermont and internationally known musicians team up for a lively two-day festival of folk and blues music performed in the pure country air of historic Plymouth Notch, birthplace of the 30th U.S. President. All concerts are free, and cash donations are appreciated.
Mad River Valley Craft Fair, Waitsfield, Vermont: September 5-6, 2026: Celebrating 55 years of fine arts and crafts, the Mad River Valley Craft Fair is a juried fair featuring eclectic Vermont gifts, clothing, and artwork. Live music is scheduled throughout the event, and the food court will keep you satiated as you look for the perfect item to take home. The $5 entrance fee supports the Valley Players.
31st Annual Mount Snow Brewers Festival, West Dover, Vermont, September 5, 2026: Welcome to the 31st Annual Mount Snow Brewers Festival, where you can sample beer and cider from dozens of brewers, enjoy fantastic culinary offerings, and dance to live music. This day-long event is perfect for all Vermont beer lovers.
Garlic Town USA, Bennington, Vermont, September 5, 2026: One of Vermont’s most popular events, Garlic Town USA in Bennington, is a celebration of all things garlic and agriculture!
Marketed as the largest family farmers’ market in the state, this is the place to stock up on garlic products, try garlic ice cream and other garlic-infused creations, and listen to fantastic live music.
Vermont Events: September 7 – 13, 2026
South End Art Hop, Burlington, Vermont, September 11-13, 2026: The 34th annual South End Art Hop in Burlington is a celebration of the creative and entrepreneurial spirit of the South End neighborhood in the city. Chat with new and established artists in the community, purchase artwork, eat good food, and explore!
Orleans County Fair, Barton, Vermont, September 10 – 13, 2026 Head to the Northeast Kingdom this year for the 159th annual Orleans County Fair. Traditional events include a demolition derby, cattle shows, 4-H events, harness racing, live music, and carnival rides.
The Third Annual Rutland Whoopie Pie Festival in Rutland, Vermont, September 12, 2026: This all-day extravaganza features live music, yoga for kids and adults, face painting, food trucks, street performers, and of course, whoopie pies. Center Street and Merchants Row will be closed for the festivities.
Read this post: 10 Cozy Cabins in Vermont for Your Fall Vacation
100+ Wonderful Ways to Experience Vermont
Whether you’re a local who has lived here for years or a visitor eager to explore, there’s always more to Vermont than most guidebooks would have you believe. Sure, you can easily find the popular tourist spots, but Vermont is so much more than that.
100+ Ways to Experience Vermont is the only guide you’ll need to find popular and obscure trails, waterfalls, attractions, museums, farms, breweries, and more. And unlike printed guidebooks, this digital guide included links to relevant businesses, articles, and event listings to make trip planning easier.
Formatted as a PDF file, this beautiful ebook is available to download on your phone, tablet, or e-reader and can be easily printed for off-grid exploring.
Vermont Events: September 14 – 20, 2026
Vermont Cheese Week throughout Vermont, September 14-20, 2026: Vermont Cheese Week is a state-wide, weeklong celebration designed to feed the fanaticism of all you cheese lovers out there. Celebrate Vermont cheese with unique learning, tasting, pairing, and local “Vermontish” experiences all over the state.
Tunbridge World’s Fair, September 17 -20, 2026: September in Vermont means a trip to Tunbridge! Celebrating 154 years in 2026, the Tunbridge World’s Fair allows you to step back in time with demonstrations of farming and agricultural traditions, working antique displays, horse and ox pulling, horse racing, cattle and horse shows, junior exhibits, floral and 4-H exhibits, contra dancing, gymkhana, and many free shows.
Burlington Baroque Festival, Burlington, Vermont, September 17-20, 2026: Celebrate the timeless beauty of Baroque music at this four-day event featuring internationally acclaimed musicians performing on period instruments. Held at College Street Congregational Church in downtown Burlington, the festival includes four unique concerts showcasing the works of Purcell, Handel, Vivaldi, and Bach. A must for classical music lovers and culture seekers.
Von Trapp Oktoberfest, Stowe, Vermont, September 19, 2026: Welcome to the 17th annual Oktoberfest at the von Trapp Brewing Bierhall at Trapp Family Lodge, featuring fantastic beer, great food, and lots of fun.
German Bands will be playing throughout the day, and there will be Trachten contests (for traditional Oktoberfest outfits), cask tapping, and a US Steinholding competition at each session.
Wine & Harvest Festival, Dover, Vermont, September 18 – 19, 2026: The 17th Annual Vermont Wine & Harvest Festival will celebrate Vermont vintners, specialty food producers, chefs, painters, publishers, cheese makers, potters, jewelers, photographers, and farmers in Vermont. The event kicks off on Friday in downtown Wilmington with a wine stroll and soup contest and moves to Mount Snow on Saturday with live music and vendors, as well as the Vermont Wildlife Festival.
Chester Festival on the Green, Chester, Vermont, September 19 & 20, 2026: For 50 years, this free annual event has kicked off the beginning of the fall foliage season. Hundreds of people converge on the historic Green in Chester from all over New England. Featuring food and craft vendors, family activities, field games, demonstrations, and live music, this is one of the loveliest ways to spend September in Vermont.
Vermont Events: September 21 – 30, 2026
Killington Brewfest at Pico Mountain, Vermont, September 26, 2026: Whet your whistle against a backdrop of Vermont’s finest autumn foliage. Enjoy live music, fabulous food offerings, and dozens of the finest craft beers in the region. Brewfest is a 21+ event and one of Killington’s most distinctive annual celebrations.
Bristol Harvest Festival, Bristol, Vermont, September 26, 2026 The 27th annual Bristol Harvest Festival will feature more than 60 craft and food vendors, live music, and sidewalk sales in one of Vermont’s cutest towns.
Old Fashioned Harvest Market, Underhill, Vermont, September 26 & 27, 2026: The Old Fashioned Harvest Market offers a full weekend of fun for all ages. Old-fashioned fun includes a parade, dunk booth, greased pole climb, a log-sawing contest, hay rides, and more.
Burke Fall Festival, East Burke, Vermont, September 26, 2026: Kick off the day with a parade at 10 am, followed by a barbecue, free ice cream, wagon rides, cow plop bingo, rubber duck races, live music, cider pressing, and a craft fair with 70+ vendors.
September in Vermont is all about celebrating the art, music, and seasonal produce that make small towns in Vermont so special. If you’re visiting Vermont in September, put one of these fun events on your itinerary!
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