Hometown Holidays 2026

Hometown Holidays downtown Middlebury

Friday and Saturday, November 20 & 21, 2026

Don’t miss Middlebury’s 33rd Hometown Holidays!

It kicks off an annual tradition held the Friday before Thanksgiving in downtown Middlebury. Locals gather downtown to shop, eat, socialize, and enjoy festive music. The Chamber will give away $2,500 in gift cards on Nov 20th, courtesy of Jayco Inc. Visit Middlebury Shops to grab early holiday deals and for a magical chance to receive a gift card from a Middlebury Shop.