Every October, Middlebury comes together to turn downtown into a stage for costumes, candy, and community.
NEW!! On the 24th of October 🎃 Help Us Spookify the Gazebo! 👻
The Better Middlebury Partnership / Experience Middlebury invites you to join us on Friday, October 24th, from 1:30–3:00 PM at Triangle Park for a fun community decorating gathering!
If you have any old Halloween decorations, pumpkins, cornstalks, hay bales, spiders, cobwebs, ghosts, ghouls, or witches lurking in your garage or attic—bring them along to help us transform the gazebo into something spookily spectacular!
It’s a day off from school, so bring your little ones (and not-so-little ones!) to join in the fun. We’re decorating in anticipation of Middlebury’s Spooktacular on Sunday, October 26th (11 AM–1 PM) with a mini parade and plenty of Halloween cheer.
THE MAIN EVENT!! SPOOKTACULAR
Spooktacular on Sunday, October 26th, 2025 is no exception—though it comes with a few playful twists, fine-tuned with families in mind.
A Parade Made for Everyone
When neighbors, shopkeepers, and volunteers gathered to plan this year’s event, one question kept bubbling up: How can we make Spooktacular even more joyful for the littlest ghosts and goblins?
The answer: a new earlier parade time—11am to 1pm—perfectly timed so little ones can march, laugh, and collect treats before nap time kicks in.
So here’s the plan:
- Families gather at the gazebo on the Middlebury green at 11:00am.
- At 11:30am, the parade takes off, led by the one-and-only Spooktacular Witch—our friendly guide who knows Main Street like the back of her broomstick.
- With the help of crossing guards, the parade will cross at the Post Office, travel up Main St to Cannon Park, cross over, Â then loop past the [under-construction] Ilsley Library before making its way back down Main Street to finish at Triangle Park by the fountain.
And of course, shopkeepers and volunteers will be ready with buckets of candy—not just along the parade route, but also on Merchants Row and in Triangle Park. We have Dave Shaw our fire 🔥 chief and his team helping to keep us all safe as we cross the road, but hold on to your little ones, never-the-less!Â
More Than Just a Parade
Because Spooktacular is more than marching—it’s about gathering, playing, and celebrating together.
- 🎶 WVTK’s vehicle will be parked at Triangle Park, spinning a festive soundtrack that sets the mood.
- 🎯 Kid-friendly yard games will be waiting in the park for restless little hands and big imaginations.
- 📸 Photo opportunities at the gazebo will help families capture those once-a-year costumes and wide-eyed smiles. We’re lucky enough to have our local friend and favourite photographer Caleb Kenna join us for the morning! So wear your best costume and get snapped!
A Sweet Community Effort
None of this would be possible without the generous donation of candy from Shaws, the Town of Middlebury and the countless volunteers and shopkeepers who bring Main Street to life. It’s truly a shared effort—a reminder that when we dream together, we can create something magical.
✨ This October, put on your costume, grab your trick-or-treat bag, and come walk with us. Whether you’re three or 83, Spooktacular is about seeing Middlebury at its best—joyful, playful, and maybe just a little spooky.