Even as summer days linger, we’re already turning our eyes to what’s coming up next in Middlebury—because around here, the planning never stops and the calendar is always full of reasons to gather.
Labor Day Weekend
👉 “Join us downtown for Middlebury’s Labor Day Weekend Sidewalk Sale—shop great deals, stroll the streets, and celebrate the end of summer with our local businesses!”
September Highlights
September kicks off with a bang:
Get tickets for a truly unique Vermont tradition—Bread and Puppet Theater, presented by Town Hall Theater and Bread and Puppet performing at the Addison County Fairgrounds Sunday, September 7 at 4:30pm (Brass Band at 4:00pm). Known for their larger-than-life puppets, pageantry, and powerful storytelling, Bread and Puppet brings an unforgettable performance that’s part spectacle, part community ritual. More highlights in September include:
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🎭 The Moth StorySLAM at Town Hall Theater on September 9th brings true stories told live from the heart.
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🚴♀️ Tour de Farms rolls into town on September 20th with a brand-new route starting and ending in Middlebury, connecting cyclists directly to our agricultural roots. Don’t forget—the Experience Middlebury pop-up market will be waiting at the finish line for riders and non-riders alike.
October Festivities
As the air turns crisp, Middlebury brings out some of its most beloved traditions:
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🍂 Fall Family Weekend (October 4th) welcomes college families into the heart of the community.
- 🏳️🌈 Pride Parade ( 11th October) shines brightly, reminding us of the creativity and inclusivity that make Middlebury unique.
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🚗 The Middlebury Car Show (October 12th) rolls into town, showcasing classic vehicles, community pride, and a reason to linger downtown.
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🍁 Maple Run Middlebury ( October 19th) Lace up, Middlebury—the sweetest race in Vermont is back! The Maple Run brings runners, walkers, and cheer squads together for a fall day full of energy, community spirit, and (of course) maple treats along the way.
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❤️ Stories from the Heart (October 25th) offers an evening of moving, personal storytelling.
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🎃 Spooktacular (October 26th), when Main Street fills with costumes, candy, and the joy of community parading together.
Why We Plan Ahead
Looking a few months down the line lets us prepare, but it also gives us the joy of anticipation. Middlebury thrives on these moments—whether it’s a line of vintage cars gleaming in the autumn sun, a heartfelt story told on stage, or a parade of witches and superheroes downtown. Our calendar reflects the heartbeat of this place we call home.
✨ Stay tuned for more updates at ExperienceMiddlebury.com, and keep an eye on your favorite storefronts and social channels. The best part of Middlebury is how we show up for one another, season after season.