Chestertown Crazy Days
Chestertown Crazy Days
Every July, the merchants of downtown Chestertown set up shop on the sidewalks for Crazy Days. They offer deeply discounted prices on their goods to make room for their holiday shipments. Shops of all kinds participate—book, clothing, jewelry, houseware, and unique gift shops.
There’s also plenty of street food to taste and a festive atmosphere to enjoy. The Chestertown Sidewalk Sale only lasts for a few days each summer. You don’t want to miss it!
Main Street Chestertown
04:43 AM - 09:43 PM, every day through Jul 25, 2026.
Main Street Chestertown
(410) 778-2991
office@mainstreetchestertown.org