Holiday magic is once again coming to Middlebury, beginning on December 1st with A Very Merry Middlebury!
We are planning a festive and fun-filled month of December, complete with visits from Santa, horse drawn wagon rides, an evening shopping night, a pancake breakfast with holiday characters, an “I Spy” contest with prizes, the Hot Chocolate Hut and free gift wrap for items purchased in Middlebury. This year’s events and promotions are still being planned– check back often for the latest information or follow Experience Middlebury on social media.
I Spy Contest, all December long
Try to find the hidden baby bear ornaments (designed by artist Ashley Wolff) in ten store windows in downtown Middlebury and be entered to win $100 in Middlebury Money. Rules and contest details will be displayed in the window of the Vermont Bookshop beginning December 1st. The contest is free.
December 1st-31st: Be Your Favorite Christmas Character
Ever wonder what you’d look like as a snowman? Or a gingerbread girl? Your family can pose for pictures with an assortment of adorable character cut-outs around town, including Santa, a nutcracker, gingerbread siblings, and snowmen. Posing with the character cut-outs is free.
Saturday, Dec. 3rd: Santa’s Arrival
Kick the holiday season off with a fun-filled morning in Middlebury. At 9:45am, welcome Santa to Middlebury as he arrives via fire truck, over the Cross Street Bridge and up Main Street, going around twice to give everyone time to see him. Then, enjoy a visit with the right jolly old elf himself at the Middlebury Community House from 10:00-12:30pm. Families can take an old fashioned horse drawn wagon ride through downtown Middlebury. Visits with Santa and the horse drawn wagon rides are both free.
Don’t leave Middlebury without doing a bit of holiday shopping. Anything purchased in Middlebury can be wrapped for free at 51 Main from 12:00-4:00pm—just show your receipt! And, of course, make time for a cozy cup of hot cocoa from the always-popular Hot Cocoa Hut in Cannon Park; just 25 cents for a cup with all the fixings! The Hot Cocoa Hut will be open from 9:30am-2:00pm.
Thursday, Dec. 8th: Midd Night Stroll
Your favorite Middlebury shops will be open late for extended shopping for Midd Night Stroll (formerly Stag & Doe Night), on December 8th. This year will once again offer tons of sales, discounts, giveaways and other special promotions, as well as free tastings of many of Vermont’s premier beverages, live performances, traditional Christmas caroling, the holiday SD Ireland truck and more surprises!
The Hot Cocoa Hut (Cannon Park) and Gift Wrap Station (51 Main) will both offer extended hours as well—everything is open from 5:00-8:00pm.
Check out this list of promotions, deals and tastings: midd-night-web-promotion
Saturday, December 10
Santa will be visiting Maple Landmark on Exchange St. from 10:00-noon; visits are free! Gift wrap will once again be offered for any item purchased in Middlebury 51 Main from 12:00-4:00pm—just show your receipt! The Hot Cocoa Hut will be open from 9:30am-2:00pm.
Reserve your tickets for the Holiday Pancake Character Breakfast, one of the best events of the year. Characters, coloring, balloons, music and a delicious pancake breakfast graciously donated by the Middlebury Inn! Tickets are on sale now with limited seating at 8:30am and 10:00am. Tickets are $12/adult and $8/kids 12 and under.
Saturday, December 17
Catch Santa Claus one last time before he heads North! He’ll be at Danforth Pewter (Seymour St. Ext) from 10:00-noon and visits are free. Grab a cup of cocoa from the Hot Cocoa Hut, open 10:00am to 2:00pm and take advantage of gift wrapping at 51 Main- free for any items purchased in Middlebury- from noon-4:00pm.
Calendar of Events
Download the full calendar of events and I-Spy sheet here: