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, 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.
https://www.downtownchestertown.org/
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.
Head out for an evening of fun in Chestertown this Thursday, November 17 for the annual Ladies’ Night, sponsored by the Downtown Chestertown Association. Shops and eateries will be open late with deals and specials for all – particularly the ladies. Many shops will be offering complimentary refreshments.
Santa will see children again on Saturday, Nov. 26 from 11am-1pm and then on the following Saturday, Dec. 3 during the Dickens of a Christmas weekend. He will also be receiving children from 11:00 a.m. until 1:00 p.m. on Dec. 10 and Dec. 17. Children will receive gift bags from Santa courtesy of Twigs and Teacups. For more information about holiday activities, visit mainstreetchestertown.org, email 
The Downtown Chestertown Association (DCA) is once again sponsoring a scarecrow meter contest to decorate downtown sidewalks for Halloween.
Join in on the fun and wear a Crazy Hat! Shops owners are bringing back the custom of wearing crazy hats for Crazy Days. You might just win some Chestertown Cash for your chapeau.
Head out for an evening of fun in Chestertown this Thursday, November 18 for the annual Ladies’ Night, sponsored by the Downtown Chestertown Association. Shops and eateries will be open late with deals and specials for all – particularly the ladies.
Downtown Chestertown shops, restaurants and galleries are looking forward to seeing everyone this Easter weekend. Businesses will be open late, until at least 7 pm, in celebration of April 2, First Friday. In addition, the Downtown Chestertown Association is hosting an Easter Eggscapade. Kids of all ages can enjoy hunting for treasure filled eggs at shops both Friday and Saturday. Participants include Bad Alfred’s Distillery, Bee Crafty, Bookplate, Chester River Soaperie(in the Farmers’ Market), Coco’s Pet Center, Houston’s Dockside Emporium, Les Poissons Gallery, Riverside Unique, Sarah Paige Studio Salon, The Finishing Touch, Tish Fine Art Plus, and Twigs & Teacups. As the Easter Bunny can be crafty, it pays to look around outside the shops as well. There might be some eggs hiding along the sidewalks.
Downtown Chestertown invites everyone to show their state pride in celebration of Maryland Day, Thursday March 25 through Sunday, March 28. Shops and businesses will be all be flying the state flag. Wear your Maryland hat, scarf, jacket, mask… and receive VIP pricing at these participating downtown locations: Bad Alfred’s Distillery, Bee Crafty, Bookplate, Figg’s Ordinary, Houston’s Dockside Emporium, Les Poissons Gallery, Riverside Unique, Sarah Paige Studio Salon, The Finishing Touch, Tish Fine Art Plus, Twigs & Teacups.
Downtown Chestertown invites the community to join them in honoring Black history this First Friday, February 5 and throughout the month with creative and educational displays and exhibits. As usual, shops and galleries will have extended hours on First Friday, February 5.