If you’ve ever wondered what Halloween in Redding, Connecticut feels like, picture crisp fall air, pumpkin-lined driveways, and neighbors gathering to celebrate the season. Redding may be known for its spacious properties and scenic open space, but come late October, our quiet town comes alive with community spirit and a touch of spooky fun.
👻 Trunk or Treat at the Redding Community Center
The Halloween celebrations kick off the Saturday before Halloween with the beloved Trunk or Treat event at the Redding Community Center, hosted by the Redding Neighbors & Newcomers. Families decorate their car trunks in creative themes, kids parade through in costume, and everyone enjoys music, treats, and festive fun. It’s the perfect small-town event that showcases what makes living in Redding so special — community connection and creativity!
🎃 Jack-O’-Lantern Display on the Town Green
Every year, the Redding Garden Club invites residents to drop off their carved pumpkins for a spectacular Jack-O’-Lantern display on the town green. As dusk falls, dozens of glowing faces light up the night, creating a charmingly eerie scene straight out of a storybook. It’s a wonderful stop for families looking to soak in some local Halloween magic.
Pumpkin Picking at Warrup’s Farm
Need a pumpkin to carve? Head over to Warrup’s Farm, Redding’s very own working farm. You’ll find pumpkins, gourds, and other fall favorites, all set against a beautiful countryside backdrop. It’s the perfect weekend outing to embrace the season — whether you’re decorating your porch, carving a masterpiece, or sipping warm cider while your kids explore.
🧛♀️ The RN&N's Annual Adult Costume Party
Halloween in Redding isn’t just for the kids! Each year, The Redding Neighbors and Newcomers host a lively Adult Costume Party at The Granite that channels the same energy as the iconic town hall scene from Hocus Pocus. Locals trade trick-or-treat bags for cocktails, music, and creative costumes that range from glamorous to ghoulish. It’s become one of the most anticipated events of the season — a night of laughter, dancing, and small-town mischief that reminds everyone why Redding’s community spirit runs deep, even after dark.
🏡 Trick-or-Treating in Redding
Living in Redding means larger lots and peaceful country roads, which can make traditional door-to-door trick-or-treating a bit tricky. But our town has its traditions! Families often gather in cul-de-sacs and circular neighborhoods for safe, spirited fun.
The most famous spot? Drummer Lane — where the police close off the road, residents go all out with incredible decorations, and the entire community pitches in to donate candy for the hundreds of visitors who come by each year. It’s Redding’s unofficial Halloween headquarters!
Other great trick-or-treat streets in Redding include:
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🕸 Deer Hill Road
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🍬 Orchard Drive
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👻 Pine Mountain Road
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🎃 Portland Avenue
Each neighborhood adds its own spin — from haunted driveways to friendly fire pits and music — creating an unforgettable Halloween experience for kids and adults alike.
Why We Love Halloween in Redding
Halloween here isn’t just about costumes and candy. It’s about community, creativity, and connection — values that make Redding such a wonderful place to live year-round. Whether you’re new to town or have called Redding home for decades, these local traditions remind us how special our small-town life truly is.
Thinking about making Redding home?
As a local Realtor who lives and works right here, I’d love to help you discover the neighborhoods that make this town so special — in every season.
