Every December, Middlebury glows — with lights, with laughter, with cocoa, with kindness, and with that unmistakable small-town sparkle that a community like ours can create with some imagination and a whole lot of collaboration. But behind every wreath, every tree, every carol, every cocoa cup, and every beautifully lit moment is a tremendous amount of quiet, joyful work.
A Very Merry Middlebury doesn’t simply “happen.” It is woven together by volunteers, makers, business owners, town partners, musicians, artists, and a whole constellation of people who show up — again and again — to make sure our downtown feels warm, welcoming, and full of wonder.
For starters, this year’s beautiful holiday tree — donated by the Franklin family and chosen with care and raised into place by our incredible Middlebury Public Works team — is a perfect reminder of how much heart, coordination, and community spirit goes into making our town shine. Not to mention the creative lighting at the roundabout by the Town Offices…this hardworking team bring flair and creativity to all they do ✨ STARS one and all ✨
This year, over 40 wreaths will be lovingly decorated by the Better Middlebury Partnership Board and friends this weekend — a true labor of love that sets the tone for everything else that follows. And that’s just the beginning.
As we head into A Very Merry Middlebury 2025, coming in HOT (and COCOA-hot!), here’s everything you need to know so you don’t miss a moment of the magic. Get these dates in the diary, tell your people, and be prepared!
✨ Key Dates & Festive Happenings
-
Henry Sheldon Museum — Wreath & Tree Fundraiser all season + Holiday Trains (Nov 28–Jan 3)
-
December 1 — Maiden Vermont at THT, 7pm
-
December 4 — Very Merry Middlebury Midd Stroll
-
Late-night shopping 5–8pm
-
Tree Lighting at 6pm in Triangle Park
-
Craft Fair at the THT Anderson Wing, 5–8pm featuring beloved local artisans:
Catie of Foxglove, Yinglei Zhang, Jen Roberts, Jill Florence Brooks, Colleen Wilcox, Emma Ranney, and Katie O’Connell -
(More information at Middlebury Studio School)
-
-
A Christmas Carol at Town Hall Theater — Dec 5–7 & 11–13 (see THT website for full details)
-
December 6 — Santa & Mrs. Claus at the THT, 9:30am–11:30am
-
Carriage Rides 10–12 from MCMC by the Post Office
-
Henry Sheldon Open House all day
-
Also open late Dec 4 and 11
-
Middlebury Community Music Center FREE demo classes: Music Together® & Rhythm Kids® at 9:30am and 10:30am
-
-
December 7 — Happy Hour at Jean’s Place Lounge from 4:30pm
-
Followed by the beloved Ted Perry Holiday Trio with special guest Ryan Montbleau in the Anderson Wing, 5:30–6:45pm — with the town twinkling below
-
-
December 11 — Midd Stroll + Craft Fair
-
5–8pm at the National Bank of Middlebury
-
-
December 19–21 — Night Fires Solstice Shows at THT
-
December 31 — Fireworks at Mary Hogan Fields
-
Hot Cocoa Hut — Dec 4, 6, 11, 13 & 20
-
Holiday Chocolate Bar Raffle — $2,500 in local prizes!
And All December Long…
✨ Twinkling lights
✨ Glowing falls
✨ Rudolph the Snowplow
✨ SD Ireland Holiday Truck
✨ Festive shop windows
✨ Carols, cheer, and community joy
Let’s make December magical — together.
With love, K & K 🎄✨