Annual Events

Events are a THING again! But, not every event is happening, and some events are taking different shapes than previous years. Visit each event’s website to get the most up-to-date information.

All year long, Middlebury is home to great events planned by local businesses and organizations, many of which are free or low-cost. Outdoor movies under the stars, a festive parade down Main Street, a food truck festival with great live music…these are all events you can experience for yourself right here in Middlebury every year. Check them out!


Canceled for 2021
Food truck festival featuring live entertainment

Festival on the Green
A week-long free concert series on the town green

Sheldon Museum Pops Concert
Fireworks and concert to celebrate the 4th of July

St Stephen’s Peasant Market
The area’s largest flea market and rummage sale

Lion’s Club Auction
Auction and BBQ on the green

Downtown Block Party
A festive party on the closed off streets of Downtown Middlebury

Middlebury New Filmmakers Festival
A four-day event celebrating new filmmakers


Trick-or-Treating down Main Street

Turkey Trot
Scenic 5k and 10k before Thanksgiving


Middlebury’s celebration of all things winter

Very Merry Middlebury
A month-long celebration of the holidays

Midd Night Stroll
Extended evening shopping, tasting and strolling


Middlebury Maple Run
Canceled for 2021
A half marathon and fun run with the sweetest views

Memorial Day Parade
Marching bands, floats and more down Main Street