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 5, 2025 | Experience, Retail, Shop
There’s something truly special about shopping in Middlebury — a town where nearly every storefront tells a personal story. Our downtown is filled with independent, owner-run shops where the people behind the counter are also the ones curating the shelves, creating...
Oct 4, 2025 | Experience, Play, Reflections, Retail, Shop
Big thanks to everyone who turned out for Fall Family Weekend today—sweet vendors, new and old connections, friends and visiting families, and students! Lots of students downtown!  The autumn sun showed up right on cue, making College Park the perfect gathering spot...
Oct 2, 2025 | Experience, Reflections, Retail
This summer, Kelly and I met up with Spencer — a rising senior at Middlebury Union High School — to talk about his passion for business, storytelling, and community. Between classes, sports, and running his own venture, Spencer’s schedule is packed, so we’re extra...
Sep 23, 2025 | Experience, Retail, Shop
We are working with Spencer Copeland, a senior at Middlebury High School, who has started a business called Local Trove ( more info to follow). Over the summer, Spencer started a series of interviews with our local businesses, and Becky was the first person he spoke...
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...
