Annapolis Scarecrow Stroll

Welcome to the 4th Annapolis Scarecrow Stroll! Scarecrows will line the streets of downtown Annapolis on West Street, Maryland Avenue, and Main Street. Deadline for entry is Friday, October 17, 2025. Check-in will be in front of Annapolis Collection Gallery on Thursday, October 23, 4:00 pm – 6:00 pm. At check-in you will receive a name tag, pole assignment, and ties to secure your scarecrow. The Annapolis Scarecrow Stroll is hosted by the Inner West Street Association in partnership with Maryland Avenue, State Circle Association, and Downtown Annapolis Partnership.

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