Oct 30, 2025 | Experience
Mark your calendars for our Small Business Weekend in Middlebury — November 28th, 29th, and 30th. The heart of downtown comes alive with holiday spirit and community pride. It’s the perfect time to explore local shops, discover unique gifts, and support the businesses...
Oct 30, 2025 | Experience
🎄✨ Merry Middlebury Kicks Off in Dec! Now that Spooktacular is done and dusted for the year ( it was AMAZING to see what we estimate to be around 750 children on Sunday!)…we’re now turning our sights (and our sparkle!) toward Merry Middlebury — one of our...
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 24, 2025 | Experience
As we start to plan beyond the current season, we look forward to a time where Middlebury truly lights up! Merry Middlebury is the result of months of thinking, planning, and coordinating with so many wonderful people — volunteers, local businesses, the Town Office...
