Mark your calendars for Downtown Chestertown’s annual sidewalk sale, Crazy Days! The bargain shopping begins on Thursday, July 27 and runs through Saturday, July 29, with many stores carrying the specials into Sunday. The shops will be open by 10 am and remain open on Thursday and Friday until 7pm, Saturday until 5pm. This mid-summer tradition is sponsored by the Downtown Chestertown Association, (DCA).
This year the DCA is reviving a popular family fun tradition – the Ping Pong Ball Drop. On Saturday, July 29 at 10 am a bucket of Ping Pong Balls will be dropped from a Chestertown Volunteer Fire Company ladder truck downtown. The balls will contain discounts and freebies at participating downtown shops. These specials will be honored just through Sunday July 30. Some lucky shoppers will win Chestertown Cash. Listen for the siren!
Great deals can be found on everything from men’s and women’s fashions, children’s clothing and toys, jewelry, home décor, crafts, kitchen items, books, artwork, art supplies, pampered pet must-haves and even musical instruments.
Eateries are posting “Crazy Days” specials, and the Animal Care Shelter for Kent County will offer hot dog lunches from 11 am to 3 pm all three days. The DCA will be selling beer and cider Friday evening and Saturday afternoon and handing out free popcorn all 3 days.
Your Downtown Chestertown independent businesses look forward to seeing you – and happy shopping!
The Downtown Chestertown Association (DCA) is a non-profit, member based organization dedicated to promoting businesses and professional services in and around Chestertown through activities that encourage residents and tourists to visit and shop locally. https://www.downtownchestertown.org/




During three of its Playmakers camp days next week, the Garfield Center will host special performances by Maryland arts educators/performers for the Playmakers camp kids to enjoy. The events are also open to the public for a small $5.00 admission fee. All proceeds from ticket sales goes back into the Garfield Center’s youth education programs, including Playmakers.
All weekend, the whole town will be in the pirate spirit as merchants, re-enactors, musicians, and other performers take you to the Golden Age of piracy on the high seas. Main Street will be alive with vendors, music, pirate performers, and plenty of grub and grog. Jumpstart the weekend on Friday with a Rum Tasting and Sea Shanty Sing-A-Long. Dine at one of the many award-winning restaurants, settle in, and enjoy the night’s live entertainment offered by some of the town’s local watering holes, or just relax under the stars. On Saturday afternoon, visit Rock Hall Harbor for a magnificent view of the Chesapeake Bay, and be sure to get your dinghy or small boat decorated for the Decorated Flotilla and Pirate Poker Run. Rock Hall’s public beach will be home to the annual Beach Party featuring music by Jah People and Soundproof. Pirate attire is strongly encouraged! Before the party begins, kids are encouraged to come and plunder the treasures of Graybeard on Rock Hall’s beach. The tradition of the perpetual Graybeard’s trophy continues and will be handed down to the Best Decorated Boat. Don’t forget to get your raffle tickets for a chance to win lots of local treasure! Tickets can be purchased at the Beach Party, Sea Shanty Sing Along on Friday and on Saturday on Main Street, and the Buccaneer’s Ball. The drawing for the treasure will be held on Saturday evening and you don’t have to be present to win. Proceeds go back to support local non-profits. Official Pirates and Wenches souvenir merchandise will be available for purchase during the weekend at the Sea Shanty Sing A Long, on Main Street, and the Beach Party. They’re sure to go fast, so get them while supplies last!




Photo: Brayden Wallace, student member of the Kent County Board of Education, receives a certificate of recognition for his service at his final meeting, May 22. From left are board members Frank Rhodes and Francoise Sullivan, Superintendent Dr. Karen Couch, board member Aretha Dorsey, Wallace and board members Trish McGee and Joe Goetz.
The Bookplate is continuing their