✨ Discover Middlebury.
Middlebury is alive with color, community, and celebration each October, and this year brings new and traditional favorites. Whether you’re a longtime resident, a student, or a visitor, there’s something happening in town for everyone. From parades to performances, markets to marathons, the calendar is bursting with activity.
🎉 October Highlights
- 🍂 Fall Family Weekend — October 4
College Park comes alive with family-friendly fun, food, and activities that celebrate autumn in Middlebury. Maple Landmark has an open afternoon the same day, so pay them a visit for all your novel gift needs. - 🌈 Pride Parade & Festival — October 11
Join us for a day of joy, inclusion, and color as Pride takes over downtown. And don’t put your walking shoes away just yet— - 🚘 The 4th Middlebury Classic Car Show and Fall Festival — October 12: Middlebury’s streets shine with chrome and nostalgia as classic cars roll in for a beloved community tradition.
- 🏃 The Maple Run — October 19
One of Vermont’s most scenic races, the Maple Run showcases the best of Middlebury’s fall beauty while bringing runners and supporters together. - 🏡 Middlebury College’s Homecoming weekend 10/24-26
- 💖 Stories from the Heart — October 25
At St. Stephen’s Church and the Henry Sheldon Museum, this moving evening blends storytelling and history to celebrate the heart of our community. - 🎃 Spooktacular — October 26, 11 AM–1 PM
Triangle Park turns festive with costumes, candy, and family fun as Middlebury gets into the Halloween spirit.
🖼️ New at the Sheldon Museum
This fall, the Henry Sheldon Museum debuts a powerful exhibition honoring Vermont’s female farmers—celebrating their stories, resilience, and contributions to our state’s agricultural history.
🎶 Sunday Afternoons at Town Hall Theater
The PM Sundays series, curated by Don Sheldon of Valley Stage Productions, brings world-class songwriters and musicians to the intimate Anderson Studio. These unforgettable Sunday performances are the perfect way to cap off a fall weekend.
From live music to local history, parades to pumpkin displays, Middlebury in October is a town brimming with creativity and community. Explore it all through Experience Middlebury and refer to relevant websites for for full details.
This season, we’re falling in love with Middlebury all over again! 🍁