Oct 26, 2025 | Experience, Kids, Play
What an absolutely spooktacular day in downtown Middlebury. On Sunday, the heart of our town filled with laughter, costumes, candy, and community spirit as approximately 800 children and families joined us for this year’s Halloween celebration. From the moment the...
Oct 16, 2025 | Experience, Kids, Play
A community call from the Better Middlebury Partnership & Experience Middlebury There’s magic in the air next week in Middlebury — a little nip of fall, a swirl of leaves, and the promise of Halloween fun ahead. And what better way to celebrate than by coming...
Oct 6, 2025 | Experience, Kids, Play, Retail
🚗 Middlebury Car Show and Fall Festival — Sunday, October 12 Main Street | 10:00 AM – 3:00 PM Over 75 classic and collector cars will roll into downtown Middlebury for a day of chrome, conversation, and community. Stroll Main Street, meet the proud owners, and enjoy...
Oct 2, 2025 | Experience, Kids, Play
Every October, Middlebury comes together to turn downtown into a stage for costumes, candy, and community. NEW!! On the 24th of October 🎃 Help Us Spookify the Gazebo! 👻 The Better Middlebury Partnership / Experience Middlebury invites you to join us on Friday, October...
Sep 21, 2025 | Experience, Kids, Play, Shop
✨ 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...
Sep 18, 2025 | Dine, Experience, Kids, Play, Retail, Retail Dine, Shop, Stay
As we start to plan beyond the current season, we look forward to a time where Middlebury truly lights up! Very Merry Middlebury is the result of months of thinking, planning, and coordinating with so many wonderful people — volunteers, local businesses, the Town...
