Celebrate Autumn in Vermont: 6 Unforgettable Fall Festivals You Won’t Want to Miss

October is peak foliage and the perfect time to enjoy fall harvests, events, and festivals

As the Green Mountains blaze with fiery reds and golden yellows, Vermont transforms into a living postcard—and there’s no better way to soak it all in than by joining the locals at one of these seven uniquely Vermont fall festivals. Make Cooper Hill Inn your home base for the weekend (or week!) as you explore picturesque local communities and celebrate the changing of the seasons with spectacular displays of fall color. Whether you're into crafts (arts & brews), vegetal catapults, or the beauty of nature, these events may inspire you to hit the road and revel in the season.

1. Hildene Farm Autumn Harvest Festival – September 26, 2025

Delicious food, pumpkin picking, live music, and all the seasonal vibes you'd want from a community fall gathering. Advance purchase of tickets required. ***Tickets will not be available at the event.*** Set against the stunning backdrop of Hildene. Festival Tickets: Adult Admission $8, Youth 13-17 $2,Children 12 and under FREE, Weekend pass $10,Students $5 with ID.

2. The Peru Fair – September 27, 2025

Step back in time at this old-fashioned country fair in the picturesque town of Peru. Rated among Vermont’s top fairs, it features artisan booths, farm animals, traditional food, and a warm, nostalgic vibe that draws crowds year after year.

3. Vermont Pumpkin Chuckin’ Festival – September 28, 2025

Yes, you read that right—pumpkin chuckin’! Head to the Stowe Events Field to watch homemade trebuchets and catapults launch pumpkins through the crisp autumn air. It’s quirky, it’s loud, and it’s all for a good cause: proceeds benefit the Clarina Howard Nichols Center.

4. Vermont Sheep & Wool Festival – October 4–5, 2025

Cozy up at this fiber-lover’s paradise in Tunbridge. With over 70 vendors, workshops on knitting, spinning, and dyeing, plus sheep shearing and dog herding demos, it’s a celebration of all things wooly and wonderful. Admission: $10 a day for adults, $5 for children under 12, toddlers are free.

5. Billings Farm Harvest Celebration – October 4–5, 2025

Located in Woodstock, this hands-on harvest fest invites you to press apples, bowl with pumpkins, and sample seasonal treats. It’s a wholesome, interactive experience perfect for families and foodies alike.

6. Newfane Heritage Festival – October 11–12, 2025

For over 50 years, this beloved event has brought together artists and craftspeople on the Newfane town common for a day of community and fall favorites. It’s a celebration of heritage, handmade goods, and hometown spirit—right at the height of fall color.