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September in Vermont: 20 Festivals to Kick off Fall in 2023

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.

A collage of photos featuring September in Vermont.
Experience September in Vermont! Photos by WickedVT and a-birdie

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: August 25 – September 3, 2023

Champlain Valley Fair, Essex Junction, Vermont, August 25 to September 3, 2023: The Champlain Valley Fair has been a Vermont institution for the past 101 years! This spectacular Vermont event lasts for a full 10 days, with too many special events to list.

This year’s grandstand includes Riley Green on September 3, as well as a freestyle motocross show, a huge demolition derby, and a monster truck show.

The Champlain Valley Fair in Vermont by WickedVt.
Champlain Valley Fair. Photo credit

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!

28th Annual Mount Snow Brewers Festival, West Dover, Vermont, September 2, 2023: Welcome to the 28th 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 2, 2023: One of Vermont’s most popular events, Garlic Town USA in Bennington is a celebration of all things garlic and agriculture!  Garlic Town USA, formerly known as the award-winning Garlic Fest announced that the festival will return to downtown Bennington for the 2023 Labor Day weekend.

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.

Garlic Town USA in Bennington, Vermont
Garlic Town USA is Bennington’s largest event. Photo credit

Plymouth Folk and Blues Festival, Plymouth, Vermont, September 2 and 3, 2023: The 18th Plymouth Folk and Blues Festival was selected in 2023 by the Vermont Chamber of Commerce as a “Top 10 Fall Event.” This outdoor festival takes place at Calvin Coolidge State Historic Site and features renowned musicians from both Vermont and the world stage. This event is completely free, but donations of non-perishable food items are appreciated.

Mad River Valley Craft Fair, Waitsfield, Vermont, September 2 and 3, 2023: Celebrating 52 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.

Vermont Events: September 4 – 10, 2023

Montpelier, Vermont in September.
September in Montpelier, Vermont

Orleans County Fair, Barton, Vermont, September 6 – 10, 2023: Head to the Northeast Kingdom this year for the 15th annual Orleans County Fair. Traditional events include a demolition derby, cattle and shows, 4-H events, harness racing, live music, and carnival rides.

South End Art Hop, Burlington, Vermont, September 8 – 10, 2023: The 31st annual South End Art Hop in Burlington is a celebration of the creative and entrepreneurial spirit of the South End neighborhood of the city. Chat with new and established artists in the community, purchase artwork, eat good food, and explore!

Vermont Golden Honey Festival, Proctorsville, Vermont, September 9, 2023: Celebrating its 11th anniversary, the Vermont Golden Honey Festival has been repeatedly voted one of the “Top 10 Fall Events” by the Vermont Chamber of Commerce.

Part farmers’ market, part craft fair, each Vermont vendor features a bee theme. Eclectic offerings include honey apple pizza, honey gin, beeswax balms and soaps, kombucha, mead, caramel sauce, and other honey and bee-related foods and crafts.

A apiarist holds a bee hive section with bees on it.
Celebrate the honey bee at the Vermont Golden Honey Festival!

Taste of Montpelier Food Festival, Montpelier, Vermont, September 9, 2023: Located in downtown Montpelier, this energetic (and delicious) food festival features food trucks, restaurant tastings, a corn roast, a farmers’ market, chef demos, and a parade featuring world-class street performers.

Read this post: 10 Cozy Cabins in Vermont for Your Fall Vacation

Vermont Events: September 11 – 17, 2023

Tunbridge Worlds Fair, September 14 -17, 2023: September in Vermont means a trip to Tunbridge! Celebrating 151 years in 2023, 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.

An informational sign for the Tunbridge World's Fair.
Tunbridge World’s Fair sign. Photo credit

von Trapp Oktoberfest, Stowe, Vermont, September 17, 2023: Welcome to the 14th annual Oktoberfest at the von Trapp Brewing Bierhall at Trapp Family Lodge featuring fantastic beer, great food, and lots of fun.

The Inseldudler band 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. 

Smuggs FallFest, Jeffersonville, Vermont, September 15 & 16, 2023: Spend a beautiful fall weekend enjoying live music, craft beer, and local food at Smugglers’ Notch in Jeffersonville. Two nights of live music, craft beer, and local food vendors in a gorgeous setting. More details TBA.

Chester Fall Festival, Chester, Vermont, September 16 & 17, 2023: For more than 40 years, this free annual event has kicked off the beginning of 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 18 – 24, 2023

Several people sit on the grass enjoying a glass of wine in Vermont.
Celebrate September in Vermont with good food and great wine!

The Peru Fair in Peru, Vermont, September 23, 2023: Celebrating 40 years in 2023, the Peru Fair celebrates local crafts, incredible food, and a beautiful 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.

Wine & Harvest Festival, Dover, Vermont, September 22 – 23, 2023: The 14th 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.

Old Fashioned Harvest Market, Underhill, Vermont, September 23 & 24, 2023: 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.

Bristol Harvest Festival, Bristol, Vermont, September 23, 2023: The 24th 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.

19th Century Apple & Cheese Harvest Festival, Strafford, Vermont, September 24, 2023: 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.

Vermont Events: September 25-30, 2023

Burke Fall Festival, East Burke, Vermont, September 30, 2023: 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.

Killington Brewfest at Pico Mountain, Vermont, September 30, 2023: Wet your whistle with a backdrop of Vermont’s finest autumn foliage and 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.

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!

Did we forget something? Send us an email and we’ll add it to our list!

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A collage of photos featuring the best things to do in September in Vermont.
Come celebrate September in Vermont!

Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.