Crazy Days

Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Re!magined Runway

Chester River Yacht & Country Club 7738 Quaker Neck Rd, Chestertown, MD, United States

RiverArt’s fabulous, fun and festive annual gala is returning to the Chester River Yacht & Country Club and sure to be as exciting as last year's. Come celebrate the arts with a great show, lively crowd, dinner, drink and music. Peruse our novel silent auction and ogle the outfits in our wild runway extravaganza. Better […]

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Legacy Day

Legacy Day – a festival that celebrates the rich cultural heritage of African Americans in Kent County – has occurred each August for the past ten years. It is offered free of charge to the public, thanks to the sponsorships of individuals and organizations. This event is produced by Sumner Hall with the Historical Society […]

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!