CHESTERTOWN — The Downtown Chestertown Association and the Chestertown Arts and Entertainment District are collaborating again for a set of fun, creative contests to decorate downtown sidewalks for Halloween with scarecrows and carved pumpkins.

According to a news release, scarecrow competition entrants will be assigned a specific parking meter to decorate between Oct. 23 and 26. They will stay up through Nov. 6.

No political messaging allowed.

Email downtownchester for entry form and more information or call 443-480-1987.

Carved pumpkin entrants will deliver their entry to the Finishing Touch, 311 High St., between 9:30 a.m. and 5:30 p.m. Thursday, Oct. 28 with their completed entry form.

Request an entry form by email at or by filling out a form at the Finishing Touch.

All entries will be displayed on downtown sidewalks from 5 to 10 p.m. Friday and Saturday, Oct. 29 and 30.

The Chestertown Mayor and Council will serve as the judges.

The top three scarecrows will be awarded $100 each. There are two categories for the pumpkins, free hand carved and stencil carved. The awards for both categories are $100 for first, $75 for second and $50 for third.

The list of winners of each contest will be announced at the Halloween parade, Saturday, Oct. 30, posted in the window at the Finishing Touch and listed on social media channels.

Join in the fun and start designing now, the release states.

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