• A Dickens of a Christmas

    Downtown Chestertown 200-300 High Street, Chestertown, MD, United States

    Step back in time and experience the magic of the holiday season at A Dickens of a Christmas! Our charming downtown will be transformed into a Victorian winter wonderland filled with carolers, holiday markets, carriage rides, and festive cheer. Stroll the streets, sip hot cider, and enjoy a celebration straight out of a classic storybook. […]

  • Small Business Saturday

    Downtown Chestertown 200-300 High Street, Chestertown, MD, United States

    Shop Smart, Shop Small. Show your love for your local, independent businesses and do your holiday shopping in Downtown Chestertown.  

  • Ladies Night Out – Downtown Chestertown

    Downtown Chestertown 200-300 High Street, Chestertown, MD, United States

    Downtown Chestertown businesses have had extended hours, refreshments, and special discounts for your holiday shopping needs.