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Very Merry Middlebury

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Very Merry Middlebury
MiddleburyVT 05753
(802) 598-1696

Ages: 0 and up

Cost: Free - Most Events are Free or mininimal cost.

Parking: No


The Better Middlebury Partnership’s Very Merry Middlebury committee is planning a festive and fun-filled month of December, complete with visits from Santa, horse and wagon rides, Stag and Doe night, a breakfast with holiday characters, an “I Spy” contest with prizes, the Hot Chocolate Hut and free gift wrap for items purchased in Middlebury. 

December 1-31: I Spy 10 Tiny Gingerbread Men

Try to find the 10 tiny gingerbread men hidden in 10 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 1-31: 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 (or ladies!). Posing with the character cut-outs is free.

Saturday, Dec. 7th: 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. A juggler will be on hand to entertain families waiting in line and families can take an old fashioned horse and wagon ride through downtown Middlebury. Visits with Santa and the horse and 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. 

Wednesday, Dec. 11th: Stag & Doe Night, Sponsored by WhistlePig

Your favorite Middlebury shops will be open late for extended shopping on Stag & Doe Night. In addition to great shopping, you can enjoy restaurant and drink specials and tastings by WhistlePig, Lincoln Peak and more during your night out!  To really make it a party, we’ll have a photo booth (with props!) and a DJ playing music in Cannon Park.

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.  The tastings, gift wrap and photo booth are all free.

Saturday, Dec 14th: Visit with Santa & Character Breakfast

Did you forget to ask Santa for something on your list? Catch him again at Maple Landmark Woodcraft from 10:00am to 12:00pm! This is a free event.

Gather your family for a delicious pancake breakfast, complete with a cast of characters that include an ice princess, a gingerbread man, a penguin, a snowman and a reindeer, all sure to entertain the little ones. This event will also include balloons, a photo booth (with props!) and a placemat to color featuring all of the Very Merry Middlebury characters. There will be two seatings, at 8:30am and 10:00am. Tickets are on sale now at the Middlebury Inn, $8/adult and $5/child.

And, remember: anything purchased in Middlebury can be wrapped for free at 51 Main from 12:00-4:00pm—just show your receipt! The Hot Cocoa Hut in Cannon Park will be open from 10:00am-2:00pm; just 25 cents for a cup with all the fixings.

Saturday, December 21st: Visit with Santa

This is it—your last chance to visit Santa before he heads back to the North Pole to get things ready for the big day! See Santa one final time at Danforth Pewter from 10:00am-12:00pm. This is a free event.

And, finish up any last minute shopping in Middlebury, with free gift wrapping from 12:00-4:00pm at 51 Main for items purchased in town. (Don’t forget your receipt!) The Hot Cocoa Hut (Cannon Park) will be open from 10:00am-2:00pm, 25 cents/cup with all the fixings.

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