Very Merry Middlebury

We’re excited to see our community come together to celebrate the holidays during Very Merry Middlebury this year. Here’s a look at what we have planned:

Midd Night Strolls 
Mark your calendars for Midd Night Stroll evenings in downtown Middlebury. Come out from 5:00-8:00pm on December 1st, 8th and 15th for specials, promotions and pop-ups around the downtown.

Check out the list of promotions and activities for December 15th!

Santa and Mrs. Claus 
The downtown will be bustling on Saturday, December 3rd! First, come get your photos taken with Santa and Mrs. Claus on December 3rd from 9:00-11:00am at Triangle Park’s new plaza space. 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. While you’re at the Triangle Park Plaza, shop our kids craft market with local student vendors selling specialty items.

We’ll also be hosting free horse and wagon rides around town (board in front of MCMC) and the hot cocoa hut is back in Cannon Park and will be serving cocoa with all the fixings. Enjoy caroling at the Congregational church (10am) and stop in to see the beautiful train display at the Sheldon Museum. Don’t forget to stop downstairs at Ilsley Library for a fun holiday craft!

Midd Winter’s Night Bar
The BMP’s chocolate bar raffle is back, featuring awesome local prizes including:

  • Dinner Trio: $50 each to Fire & Ice, Two Brothers Tavern and Jessica’s at the Swift House 
  • Sweet William Vase by Danforth Pewter
  • $150 worth of floral arrangements by Middlebury Floral and Gifts 
  • $150 gift card to The Middlebury Shop (Forth N Goal) 
  • $150 gift card to Autumn Gold 

To enter, purchase a chocolate bar (available at local stores in Middlebury or reach out to the BMP via email to and enter your ticket number here, along with a way to contact you in case you’re the winner. Ticket numbers are located on the wrapper of the chocolate bar on a hot pink sticker. Good luck!

Special thanks to IPJ Real Estate for sponsoring this sale and the local businesses who donated prizes!

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. Time and other details coming soon.

Visit the Experience Middlebury community calendar for a list of events happening around Middlebury during the month!

Very Merry Middlebury is coordinated by the Better Middlebury Partnership.