The Downtown Chestertown Association and the Chestertown Arts & Entertainment District are joining forces to sponsor two decorating contests that will bring Halloween spirit to downtown sidewalks — one for parking meter scarecrows and the other for carved pumpkins.
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, October 25 through Tuesday, October 27. No political messaging will be allowed.
The Mayor and Council will act as judges, and their top three choices will each receive a $100 cash prize. The Scarecrows will stay up through Sunday, November 7 as conditions allow.
The scarecrow decorating activity is open to everyone: businesses, organizations and individuals. For more information and to register for the contest, contact email@example.com or call 443-480-1987.
Artful pumpkins and Jack-o-Lanterns!
The carved pumpkin contest is open to families, friend groups and individuals (no businesses). To enter, bring your carved pumpkin(s) to The Finishing Touch, 311 High Street, on Thursday, October 29 between the hours of 9:30 a.m. and 5:30 p.m. and make sure to include a completed entry form. Request an entry form by email at manager@Mainstreetchestertown.org or fill one out at The Finishing Touch. All the pumpkin entries will be displayed on downtown sidewalks Friday and Saturday evenings, October 30 and 31, between 5:00 and 10:00 p.m.
Cash prizes of $50, $40, and $30 will be awarded for 1st, 2nd and 3rd place winners in four categories: Scariest, Funniest, Most Creative, and Best Artistry. Members of the Arts & 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 1:00 p.m. Saturday and announced through social media channels.
Start designing that scarecrow and/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. Costumes encouraged!