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Trick or Treat on Main Street

  • Gloucester Main Street 6882 Main Street Gloucester, VA, 23061 United States (map)

Celebrate Halloween in the heart of downtown Gloucester!

On Friday, October 31, from 5–7 PM, Main Street transforms into a family-friendly destination filled with costumes, candy, and festive fun.

Our Costume Contest returns for its second year, made possible by Chesapeake Bank, with prizes awarded in five categories: ages 0–12, 13–17, 18+, groups, and pets. Sign up online in advance or onsite during the event — entries close at 6:30 PM, and winners will be announced shortly after. Participants must be on-site to win.

Don’t miss the Halloween Window Decorating Contest! Participating Main Street businesses will deck out their windows with creative Halloween displays — and you get to help choose the winner. Stop by our Trick-or-Treat station on the House of Ren lawn to cast your vote, and check our social media after the event to see who takes home the title!

Thanks to the support of the Gloucester County Sheriff’s Office, families can enjoy a safe and welcoming evening on Main Street. The road will be closed to through traffic from the Historic Court Circle to Edgehill Town Center during the event.

Want to get involved? Volunteers help make this event a success each year! If you’d like to lend a hand, sign up online or contact us at admin@mspt.org.

Bring the kids, dress up, and enjoy this community tradition that has become a favorite way to celebrate Halloween in Gloucester!

Stay updated on all of the fun details here.

Costume Contest Sign-Up Form
Volunteer Sign-Up Form
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October 26

Exhibit Dedication & Opening Reception: The History of Gloucester

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October 31

Kelsick Market’s Harvest Festival