Scarecrows, pumpkins to decorate downtown

The Downtown Chestertown Association and the Chestertown Arts and Entertainment District are reviving the parking meter scarecrow contest this year and adding a contest for pumpkin carving.

CHESTERTOWN — The Downtown Chestertown Association and the Chestertown Arts and Entertainment District are joining forces to sponsor two decorating contests that will bring Halloween spirit to downtown sidewalks.

The first one is for parking meter scarecrows, the other for carved pumpkins, according to a news release.

The scarecrow competition revives a tradition started during the tenure of Mayor Margo Bailey. Entrants will be assigned a specific parking meter to decorate with their scarecrow anytime from Sunday, Oct. 25 through Tuesday, Oct. 27. No political messaging will be allowed, the release states.

The scarecrow decorating activity is open to everyone: businesses, organizations and individuals. For more information and to register for the contest, contact or call 443-480-1987.

The Chestertown Mayor and Council will act as judges. Their top three choices will each receive a $100 cash prize.

The scarecrows will stay up through Sunday, Nov. 7, as conditions allow.

The carved pumpkin contest is open to families, friend groups and individuals. This one is not for businesses, the release states.

To enter, bring your carved pumpkins to the Finishing Touch, 311 High St., between 9:30 a.m. and 5:30 p.m. Thursday, Oct. 29. Make sure to include a completed entry form.

Request an entry form by email at or fill one out at the Finishing Touch.

Pumpkin entries will be displayed on downtown sidewalks between 5 and 10 p.m. Friday, Oct. 30 and Saturday, Oct. 31.

Cash prizes of $50, $40 and $30 will be awarded for first, second and third place winners in four categories: Scariest, Funniest, Most Creative and Best Artistry.

Members of the Arts and Entertainment District Advisory Board will serve as judges.

The list of winners of both contests will be posted in the window at the Finishing Touch at 1 p.m. Saturday, Oct. 31 and announced through social media channels.

Start designing that scarecrow or pumpkin and make plans to come downtown Friday or Saturday evening of Halloween weekend to enjoy the creations conjured up by other community members, the release states.

Costumes are encouraged.

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