Feb 3, 2026 | Dine, Eat, Experience, Play, Retail, Shop
First Fridays are back ✨Starting this February, a group of local businesses are staying open later—together—to create more chances to gather, shop, sip, eat, and run into one another downtown.It’s about community, connection, and supporting the places that make...
Nov 26, 2025 | Experience, Reflections, Retail
Small businesses are the heartbeat of Middlebury. It’s the warm greetings, the familiar faces, the careful curators of beautiful things. They’re the places where we browse slowly, chat freely, and feel connected to the people who make this town what it is. This...
Oct 8, 2025 | Experience, Retail, Shop
We welcome the Devoe’s to Main St! Just opened in downtown Middlebury, Cobweb Antiques is the lifelong dream of collector Gary DeVoe. With his wife Jill, they have turned a passion for discovery into a charming new shop filled with history and character....
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...
