We’re excited to see our community come together once again this December to celebrate the holidays during Very Merry Middlebury this year. Below is a look at what we have planned!
Want to help out? It takes many elves to make this magic happen!
Click here for a link to all Very Merry Middlebury Volunteer opportunities.
December Midd Winter’s Night Bar
The BMP’s chocolate bar raffle has become a beloved tradition and great benefit for the BMP. This year’s bar is a salted milk chocolate, sourced by our friends at Adagio Chocolates, with packaging designed by the Addison Independent and Little Pressroom.
Bars cost $10 each, with all proceeds going to benefit the important work of the Better Middlebury Partnership. Special Thanks go to IPJ Real Estate for sponsoring the costs associated with the chocolate bars so as to enable this to be an important fundraiser for our organization.
This year’s prizes were incredible!
Congratulations to the following winners of this year’s Midd Winter’s Night Bar Raffle!
- Dining Experiences in Middlebury worth over $500: Gift certificates to some of Middlebury’s finest restaurants!
- Middlebury Cultural Experiences worth over $500: Celebrating Middlebury’s independent and unique shops and experiences!
- Green Mountain Adventures Recreational package worth over $500: Play, play, play with this package of outdoor adventuring!
- Self care package worth over $500: Spa treatments and pampering products from local salons and spas!
- $500 Middlebury Money
Midd Night Strolls 2026
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, carollers, tree lighting on the 3rd Dec at 6pm on Triangle Park, gift wrapping and and pop-ups around the 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 10th, the VT Department of Transportation will be there with their light-up snow plow, Rudolph, too.
The Stroll on December 3rd is open to everyone, and is specifically marketed as Midd Kid Night —Join us at 6pm for the lighting of the holiday tree on Triangle Park!
Artisan Holiday pop-up markets! Back by popular demand, the Artisan Markets will be hosted at the Town hall Theater Anderson Wing on the 3rd and the 10th of December curated by Middlebury Studio School, plus two new craft markets at the Ilsley Library on the 12th of December 9.00am-3pm and Parks and Rec on the 19th of December 9am-3pm
Free Gift Wrapping provided by the National Bank of Middlebury available for any gifts bought downtown during the Thursday Midd Night Strolls
Click for a list of shops and business to visit during this year’s Midd Night Stroll
Craft Fair Dates
December 3 and 10 at the Town Hall Theater Anderson Wing 5-8pm ( hosted by Middlebury Studio School)
December 12 Ilsley Library 9-3pm Hosted by Middlebury Ryzes and Midd Markets
December 19 Middlebury Parks and Rec 9-3pm Hosted by Middlebury Ryzes and Midd Markets
Saturday Festivities – December 12, 2026
The downtown will be bustling on Saturday, December 12! First, come get your photos taken with Santa and Mrs. Claus on December 12 from 9am – 11 am indoors at Town Hall Theater. Children can fill out a Letter to Santa (available while you wait!) to share their wish lists and then get their photos snapped by parents or caregivers.
We’ll also be hosting Free Horse and Wagon Rides with our friend Macey around town (board in front of MCMC) from 10am to noon.
And of course the Hot Cocoa Hut is back in Cannon Park and will be serving cocoa with all the fixings from 10am to 2pm.
But we’re not the only ones hosting festive fun!
FREE Caroling on the steps of the Congregational Church
FREE access to the marvelous winter trains exhibit at the Sheldon Museum. Enjoy live music, a unique handmade ornament raffle in partnership with artist Bethany Farrell and seasonal activities in the makerspace. Dates to follow!
FREE open house and hands-on musical explorations and workshops at Middlebury Community Music Center. dates to follow!
12 December Storytime in the Ilsley Library Activity Room with Miss Tricia at 10.30am!
Hot Cocoa Hut
The ever-popular Hot Cocoa Hut will be back again this year, serving hot cocoa with all the fixings
Hot Cocoa Hut Hours to be decided. WATCH THIS SPACE!!
New Year’s Eve Fireworks
Thank you to the Middlebury Parks and Rec Dept for hosting fireworks in the rec park (near Mary Hogan) this year to celebrate the new year. Free public skating at Memorial Sports Center prior to the fireworks, too. Time and other details coming soon.
Visit the Addison Independent’s community calendar for a list of events happening around Middlebury during the month!
