Join us along Main Street (Route 66) for a spooky, ghoulish gathering. Featuring a tower of Jack-o-Lanterns, apple pie baking contest, music, vendors, food trucks and trick-or-treating!

Featured Attractions Schedule

Pumpkin carving contest - In front of douglas library (22 main st)
register your jack by 5:15 pm

Our tower of Jacks is back! Prizes for children, teens and adults with a $100 grand prize! All skill levels welcome, and you will be able to take your masterpiece home with you at the end of the night. Winner announced at 6:15 PM. Sponsored by Mosquito Shield.

Apple pie bake off - Flour Girl Cafe (12 Main St)
Register your pie by 3:30 PM

Join TTCP and The Flour Girl Bakery for an Apple Pie Bake-off. $10 entry fee. See rules, times and details in the flyer towards the end of this page.

Trick-or-treating - Main street
5:00 - 6:00 pm

Trick or treat with us along the north side of Main Street along the sidewalk, from Wall Street to Ted’s! Artisans and Vendors will not be participating in Trick or Treating during this time

Barktober Dog Jog - Church of Hope (1 Main St)
check-in at 12:30 PM, dog jog at 1:30 pm

Walk, jog, stroll or sprint for this 2.3 mile fun run, with or without your canine best friend! $25 registration fee, with prizes being awarded for best costumes. No official time. Sponsored by Hebron Veterinary Hospital.
Registration available day of run, pre-register here.

Ct Ghost Investigations - Location Tbd
4:00 PM

Find out who still haunts Old Town Hall (26 Main Street) with the CT Ghost Investigation crew and the Hebron Historical Society. Learn about paranormal investigations!

There will be 2 presentations, 3:30 PM and 5:00 PM.

LIVE MUSIC - UP AND DOWN MAIN STREET (OLD TOWN HALL, FIRE HOUSE LAWN, CENTURY 21)
3:00 - 6:00 PM

Bring a lawn chair and listen to tunes while you trick or treat up and down Main Street!

Sling Shot Monster Smash - Century 21 Field
1:30 - 6:00 pm

Try your luck smashing “monsters!” for $1 per pull, benefitting future TTCP events.

Dance Demonstration - Closed Portion Of Main Street
3:30 And 4:00 Pm

Gather along Main St. for a dance by Alyson’s School of dance! They will be doing 2 demonstrations throughout the festival.

FALL FOOD VENDORS - DOUGLAS LIBRARY LOT (22 MAIN ST)
1:30 - 6:30 PM

Fill up on fall foods with Rustic Streats, Ydanis & Co. Macarons, St. Peter’s Church, NORA Cupcakes Good Vibes Kettle Corn, Greekin’ Out, Los Mariachis, Legion Burgers, Uncle D’ Blazin’ BBQ, Frank's Wood Fired Pizza, & Wicked Sinister Smokehouse

Fire Station Events - Hebron Fire Dept - Main Street
1:30 - 5:30 Pm

The Hebron Fire Department property will be hosting a Fire Truck viewing at the Station and a bounce house back in the field. Also in their field will be Sheep in a Jeep, games by the Hebron Democrats, dance demonstrations and the Slingshot Monster Smash!…AND MORE!!!

Ted’s Plaza
1:30PM - 6:30 PM

Car show, Games & more!

Spooky Scenes With Rham Drama
American Legion
2:00PM - 6:00PM

This event is sponsored by Alyson's School of Dance.

Fire and flow
Time tbd

Date: Saturday, October 21, 2023

Time: 1:30PM - 6:30PM

Location: Hebron Town Center - Hebron, CT, 06248.

Click here for More Information