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Kent County, MD

Cross the Sassafras and the Chester or boat in on the Bay; Kent County is where waters meet the land. A rural county on Maryland’s Eastern Shore, it traces its roots back to the mid-seventeenth century. Chestertown, as the county seat, offers a thriving downtown district, which includes Washington College, one of the oldest liberal arts colleges in the country, as well as our local hospital, Chester River Health System of the University of Maryland. Our Historic District offers live theater at the Garfield Center, a multitude of art galleries, fine dining as well as casual fare, and eclectic shops featuring clothing, accessories, home decor, and much more. The award-winning bakeries, coffee shops, and booksellers allow for casual coffee and conversation. 

Fresh & Local

On Saturday mornings, we meet at Fountain Park, located in the center of town. The park is home to our nationally recognized Chestertown Farmers' & Artisans' Market, where patrons may purchase fresh flowers & produce, herb & garden plants, handmade soaps, fresh bread, homemade pies, and many other locally crafted products. Most of which are readily available on a daily basis from our local shops & farms. The well-established Natural Food Store is our resource for healthy living. 


As you leave Chestertown and venture into the bucolic countryside, you'll find an endless array of both land and water recreation - bike to Betterton Beach, kayak around Eastern Neck Island, feast on crabs at the harbor in Rock Hall, watch the eagles at Turner's Creek, sail off of Quaker Neck Landing or join the local rowing club. Just inland, play a round of golf at the Chester River Yacht & County Club, or maybe tennis at the College or paddle tennis at Worton Park. Learn to sculpt with RiverArts before dancing the night away at 98 Cannon, Harbor Shack, or Waterman's, or find your rhythm, funky or formal, at the Mainstay. Sunday brunch on the River Packet will hit the spot after such a fun-filled weekend. 


The summer season begins on Memorial Day Weekend with the Tea Party Festival in Chestertown. In June we welcome the renown National Music Festival. The 4th of July features fireworks and more over the harbors at Rock Hall, Chestertown & Worton Creek. The Pirates & Wenches invade Rock Hall in August before Harry Potter and his wizards descend on Chestertown at the end of September. Sultana wraps up the sailing season by greeting the tall ships for Downrigging Weekend then onward to Dickens Weekend and all the other events that happen throughout the year.

For a "Taste of the Town" stop by the First Friday of any month... the Chestertown shops extend their hours into the evening and you can experience this vibrant community firsthand!