September in Vermont: 20 Festivals to Kick off Fall in 2025
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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 1-7, 2025
Mad River Valley Craft Fair, Waitsfield, Vermont: 2025 dates To Be Announced. Celebrating 54 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.
Orleans County Fair, Barton, Vermont, September 4 – 7, 2025: Head to the Northeast Kingdom this year for the 16th annual Orleans County Fair. Traditional events include a demolition derby, cattle shows, 4-H events, harness racing, live music, and carnival rides.
South End Art Hop, Burlington, Vermont, September 5-7, 2025: The 33rd 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!
Vermont Events: September 8 – 14, 2025
Vermont Cheese Week throughout Vermont, September 6-13, 2025: 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.
The Third Annual Rutland Whoopie Pie Festival in Rutland, Vermont, September 13, 2025: 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.
Tunbridge World’s Fair, September 11 -14, 2025: September in Vermont means a trip to Tunbridge! Celebrating 153 years in 2025, 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.
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 15 – 21, 2025
von Trapp Oktoberfest, Stowe, Vermont, September 20, 2025: Welcome to the 16th 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 19 – 21, 2025: The 16th 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 and Sunday with live music and vendors, as well as the Vermont Wildlife Festival.
Killington Brewfest at Pico Mountain, Vermont, September 20, 2025: 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.
19th Century Apple & Cheese Harvest Festival, Strafford, Vermont (paused for 2025): Another “Top 10 Event for Fall,” the 19th Century Apple & Cheese Festival celebrates Johnny Appleseed’s birthday at Justin Morrill State Historic Site. Listen to live fiddle and accordion music, meet the farm animals, make your own cider, and play period games.
Chester Festival on the Green, Chester, Vermont, September 20 & 21, 2025: 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 22 – 30, 2025
The Peru Fair in Peru, Vermont, on September 27, 2025: Celebrating 42 years in 2025, the Peru Fair showcases local crafts, delicious food, and a vibrant community. It’s been called the “End of the World Tag Sale,” with more than 100 local vendors selling everything from kettle corn to fine furniture.
This old-fashioned country fair and street festival invites lovers of Vermont and rural life to come enjoy a wonderful fall afternoon in the Green Mountains.
Bristol Harvest Festival, Bristol, Vermont, September 27, 2025: The 26th 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 27 & 28, 2025: 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 27, 2025: 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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