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The festivities kick off Friday, October 31st, as the whole town lights up with Halloween excitement. Local businesses will stay open late, inviting trick-or-treaters and families to enjoy a safe and spirited evening downtown.Early Evening – Trick-or-treating through Kent’s Main Street as shops and restaurants open their doors for candy and spooky surprises.
5:00 PM – Kent “Trunk or Treat” in the Webster Bank parking lot on North Main Street — a family-friendly favorite where decorated cars hand out treats & Hayrides with volunteers from CAMA.
7:00–7:15 PM – Don’t miss the annual “Thriller” Flash Mob, when local students from Kent Center School, Marvelwood and South Kent School take to the Golden Falcon lot to recreate Michael Jackson’s iconic moves.
All Evening – Town-wide decorations, festive lighting, and a lively Halloween atmosphere that brings together businesses, families, and visitors from across the region.
The Main Event: Kent’s Halloween Costume Contest
At 7:30 PM, the energy shifts to 45 On Main, where the Kent Halloween Costume Contest begins.
This year’s contest is extra special — with guest judges Rob Zombie and Sheri Moon Zombie awarding prizes for the Scariest, Funniest, and Most Creative costumes across categories for Kids, Adults and Pets.
Participation is free, but attendees are encouraged to donate to the Kent Food Bank, with Rob & Sheri matching all donations dollar for dollar. Expect laughs, shrieks, and jaw-dropping costumes as the community competes for limited-edition Zombie-designed trophies.
Location: 45 On Main Coffee, 45 North Main Street, Kent, CT
Register Free: ticketsignup.io/TicketEvent/Halloween
8:30 PM – A Halloween Surprise at The Morrison Gallery
When the contest wraps up, the night isn’t over! Head over to The Morrison Gallery at 8:30 PM for a special Halloween surprise.
The gallery will open its doors with an exclusive first ever gallery showing of Rob Zombie's artwork with "WHAT LURKS ON CHANNEL X?" The exhibition will be on display from October 25th – November 16th. Zombie's paintings to be displayed are a colorful collision of pop culture iconography spanning over a decade's worth of work. This exhibition will include over 10 large scale works on canvas.
Kent’s restaurants, cafes, and shops will be open late for Halloween night. Visitors can also stay locally at one of the Inns or Boutique Lodgings.
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Event Venue & Nearby Stays
N Main St, Kent, CT 06757, United States
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