Vermont’s harvest season comes alive with small-town fairs and lively festivals. From wine-tasting in the mountains to quirky events like pumpkin chuckin’.
If you’re planning a trip this fall, here are 10 of the best harvest festivals and local fairs in Vermont this September that capture the state’s spirit of community, food, and fun.
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1. Vermont Wine & Harvest Festival – West Dover
If you’re a wine lover, this is your paradise. Held in the Mount Snow Valley, the Vermont Wine & Harvest Festival brings together local vineyards, craft breweries, and distilleries for a weekend of tastings.
Dates: Scheduled for September 20–22, 2025 (annual third weekend of September).
Tickets: Entry is ticketed, and advance purchase online is recommended.
Official site: vermontwineandharvestfestival.com
Location: Mount Snow Resort, West Dover.
Food Highlight: Look out for Vermont cheddar pairings and maple-infused wines.
Best for: Adults—great for couples and groups of friends.
Nearby Attraction: Take a scenic drive along Route 100, one of Vermont’s most beautiful fall foliage routes.
Pro Tip: Book your stay early in West Dover or Wilmington as lodging fills up fast around festival weekend.
2. Tunbridge World’s Fair – Tunbridge
A tradition since 1867, the Tunbridge World’s Fair is one of Vermont’s most iconic September events. Think carnival rides, agricultural showcases, horse pulling contests, and everything you’d expect from an old-fashioned fair.
It’s the kind of place where families and farmers come together, and you’ll see Vermont’s rural traditions in full swing.
Dates: Runs September 11–14, 2025.
Tickets: Entry fee is around $15 for adults; kids often get discounted rates.
Official site: tunbridgeworldsfair.com
Location: Tunbridge Fairgrounds, Tunbridge.
Food Highlight: Don’t miss the cider donuts and maple cotton candy.
Best for: Families—it’s one of the most kid-friendly events.
Nearby Attraction: Explore the scenic White River Valley for covered bridges and small-town charm.
Insider Tip: The livestock competitions are a local favorite—make sure you catch at least one.
3. Chester Festival on the Green – Chester
Imagine strolling along a charming New England green lined with artisan booths, live music, and local food.
That’s the Chester Festival on the Green. This arts-and-crafts fair is a must-visit for anyone who loves small-town Vermont charm.
Dates: Happening on September 21–22, 2025.
Tickets: Free entry.
Official site: chesterfestival.org
Location: The Chester Green, right in the village center.
Food Highlight: Try homemade pies and maple kettle corn sold by local bakers.
Best for: Families, art lovers, and casual travelers.
Nearby Attraction: Visit the famous Vermont Country Store in nearby Rockingham for a nostalgic shopping experience.
Insider Tip: After the festival, explore Chester’s antique shops for some hidden treasures.
4. The Peru Fair – Peru
Known as one of Vermont’s most beloved small-town festivals, the Peru Fair is all about food, crafts, and community spirit.
The highlight? The parade that winds through the heart of the village. You’ll find everything from maple cotton candy to handmade jewelry here.
Dates: Always held on the last Saturday of September—for 2025, that’s September 27.
Tickets: Small entry fee (usually around $5) goes toward local charities.
Official site: perufair.org
Location: Peru village center, just off Route 11.
Food Highlight: Maple cotton candy is a signature treat here.
Best for: Families and couples who want a cozy, authentic Vermont vibe.
Nearby Attraction: Take a short drive to Bromley Mountain for scenic chairlift rides.
Travel Tip: Parking can be tricky. Arrive early or use the designated shuttle services.
5. Bristol Harvest Festival – Bristol
Set against the beautiful backdrop of the village green, the Bristol Harvest Festival is a family-friendly favorite.
The festival features live bands, local vendors, and activities that keep both kids and adults entertained.
Dates: Scheduled for September 20, 2025.
Tickets: Free entry.
Official site: addisoncounty.com
Location: Bristol Town Green, Main Street.
Food Highlight: Freshly pressed apple cider and maple-glazed donuts are must-tries.
Best for: Families, especially with young kids.
Nearby Attraction: Hike nearby Bristol Falls or Mount Abraham for stunning views.
Pro Tip: Pair your visit with a hike to Bristol Falls or Mount Abraham—it’s the perfect day out.
6. Old Fashioned Harvest Market – Underhill
If you’re looking for that nostalgic “country fair” feel, the Old Fashioned Harvest Market in Underhill is it.
With kids’ games, community performances, and plenty of food booths, it feels like stepping back in time.
Dates: Usually the last weekend of September—in 2025, that’s September 27–28.
Tickets: Free entry, donations encouraged.
Official site: underhillharvestmarket.com
Location: Town green and surrounding roads, Underhill.
Food Highlight: Locals rave about the homemade apple pie.
Best for: Families with young children.
Nearby Attraction: Take a drive up to Smugglers’ Notch for incredible fall foliage.
Insider Tip: It’s an especially great pick for families with young children.
7. Burke Fall Festival – Burke
Tucked away in Vermont’s Northeast Kingdom, the Burke Fall Festival combines the beauty of fall foliage with small-town celebrations.
Expect a parade, farmers market, and craft vendors, all set against rolling hills just starting to show their autumn colors.
Dates: Typically held on the last Saturday of September—September 27, 2025.
Tickets: Free entry.
Official site: burkevermont.com
Location: Burke Mountain and town green.
Food Highlight: Fresh cider and maple fudge from local vendors.
Best for: Families and road trippers exploring the Northeast Kingdom.
Nearby Attraction: Combine with a scenic drive through Lake Willoughby and East Burke village.
Travel Tip: Don’t just stop at the festival—take a scenic drive through the Northeast Kingdom for some of Vermont’s best fall views.
8. Vermont Pumpkin Chuckin’ Festival – Stowe Area
Ever seen pumpkins fly through the air? At the Vermont Pumpkin Chuckin’ Festival, you will.
This quirky festival celebrates fall with live music, family games, and homemade trebuchets launching pumpkins across open fields. It’s one of those “only in Vermont” experiences.
Dates: Scheduled for September 28, 2025.
Tickets: Small admission fee (around $10), with proceeds supporting local charities.
Official site: vtpumpkinchuckin.com
Location: Stowe Events Field, Stowe.
Food Highlight: Hot cider, chili, and pumpkin-based baked goods.
Best for: Families—it’s a great mix of fun and fall entertainment.
Nearby Attraction: Visit Stowe Mountain Resort for gondola rides with sweeping foliage views.
Pro Tip: Bring your camera—between flying pumpkins and foliage in the background, you’ll get some fantastic shots.
9. Autumn on the Green – Danville
Danville’s Autumn on the Green is a classic Vermont event featuring artisan booths, maple products, and local food vendors.
The whole town green turns into a lively market, making it one of the most picturesque fall festivals in the state.
Dates: Held on the first Sunday of October, but falls in late September some years. In 2025, it’s September 28.
Tickets: Free entry.
Official site: danvillevt.net
Location: Danville Town Green.
Food Highlight: Try maple creamies and maple-frosted donuts.
Best for: Families, foodies, and photographers.
Nearby Attraction: Take a foliage drive along Route 2 toward St. Johnsbury.
Insider Tip: Don’t miss the maple-flavored treats—locals say they’re some of the best you’ll find in Vermont.
10. Billings Farm Harvest Fest – Woodstock
For a truly authentic harvest celebration, head to Woodstock’s Billings Farm.
This working farm-turned-living museum offers demonstrations of traditional harvest activities, horse-drawn wagon rides, and food tastings that highlight Vermont’s agricultural roots.
Dates: September 20–21, 2025.
Tickets: Entry included with Billings Farm admission.
Official site: billingsfarm.org
Location: Billings Farm & Museum, Woodstock.
Food Highlight: Freshly churned butter and farmhouse cheeses.
Best for: Families and anyone interested in Vermont’s farming heritage.
Nearby Attraction: Stroll through Woodstock village with its covered bridge, shops, and cafes.
Travel Tip: Woodstock itself is one of Vermont’s prettiest towns—plan some extra time to wander around after the festival.
Planning Your Vermont Festival Hopping
- Festival route idea: Start in West Dover (Wine & Harvest), head north to Peru and Chester, then circle through Woodstock and Bristol. Finish with Stowe, Danville, and Burke in the Northeast Kingdom.
- Where to stay: Small inns and B&Bs book up fast in September. Reserve early, especially near Stowe, Woodstock, and Mount Snow.
Conclusion
September in Vermont isn’t just about watching the leaves turn—it’s about experiencing community traditions that have stood the test of time.
Whether it’s sipping wine in the mountains, cheering on a parade, or watching pumpkins fly, these festivals capture the heart of Vermont in fall.
Read More: 4 Best Vermont Train Rides for Fall Foliage 2025
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