Midd Night Stroll

Mark your calendars for Midd Night Stroll evenings in downtown Middlebury. Come out from 5:00-8:00pm on Thursday, December 3rd, and Thursday, December 10th, 2026 for specials, promotions, food trucks and pop-ups downtown.

Visit Cannon Park to grab a cup of cocoa with all the works, and enjoy the festive SD Ireland cement truck, adorned with holiday lights. On the 11th, the VT Department of Transportation will be there with their light-up snowplow. Rudolph, too.

The Stroll on December 3rd is open to everyone, but is specifically marketed as Midd Kid Night — all Middlebury College students will receive Middlebury Money to spend in town! Join us at 6 pm for the lighting of the holiday tree!  Enjoy holiday favorite songs with Maiden Vermont in Triangle Park near the fountain on the 10th, with performances starting at 6pm and 7pm.

Artisan Holiday pop-up markets!

Free Gift Wrapping provided by the National Bank of Middlebury available for any gifts bought downtown during the Thursday Midd Night Strolls