Crazy Days Ahead! July 25 – 27, 2024

Mark your calendars for Downtown Chestertown’s annual sidewalk sale, Crazy Days! The bargain shopping begins on Thursday, July 25 and runs through Saturday, July 27, 2024 with many stores carrying the specials into Sunday. The shops will be open by 10 am and remain open on Thursday and Friday until 6 pm, Saturday until 5 pm. This mid-summer tradition is sponsored by the Downtown Chestertown Association, (DCA).

On Saturday there will be several family friendly activities, beginning with the second annual Ping Pong Ball Drop. At 10 am on Memorial Row, a bucket of Ping Pong Balls will be dropped from a Chestertown Volunteer Fire Company ladder truck. The balls will contain discounts and freebies at participating downtown shops. These specials will be honored just Saturday July 27 and Sunday July 28. Limited to only one Ping Pong Ball redemption per shop – please.

The popular ‘Bubble Dad, ’sponsored by Main Street Historic Chestertown will set up in Memorial Row after the Ping Pong Ball Drop. In addition, there will be Free Face Painting from 10 am to 1 pm.

Phoenix Martial Arts will offer 3 demos in Fountain Park: at 10:30 am Forms, weapons at Noon, and self defense at 1:30 pm. The Chestertown Recreation Committee will have Jenga and Connect 4 games from 10 am to 2 pm.

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 2 pm all three days. McGruff the Crime Dog will be making an appearance as well – as long as it is not too hot!

Your Downtown Chestertown independent businesses look forward to seeing you – and happy shopping! Thank you to our partners in this event– Main Street Historic Chestertown and the Chestertown Recreation Committee.

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.

Welcome!