About the event 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 55 West Street, Thursday, October 23rd, 4-6pm. 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 and State Circle Association and Downtown Annapolis Partnership. Register for Annapolis Scarecrow Stroll 2025 now! Check out some of these from 2024 Scarecrow Stroll