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, 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 the healthy living.
Located 27 miles directly across from Baltimore's Inner Harbor, Tolchester Beach was a thriving Chesapeake Bay resort in the 19th century. Baltimore city residents traveled across the Bay by steamboat Louise to celebrate summer where they enjoyed roller coaster rides at the amusement park, shooting at the range, dancing in the pavilion, swimming at the sandy beach and sunbathing, and renting boats to fish and crab. The park's hotels and restaurants would certainly accommodate those who desired an extended stay. As the Bay Bridge made it convenient for vacationers to get to the Ocean, Tolchester began to decline. By the time Louise was retired by the Tolchester Steamboat Company in the 1920's, she will have transported 5 million passengers. The amusement park officially closed in 1962.
Today, Tolchester Estates is a private community that serves as home to many second-homeowners and full-time residents who appreciate the water-oriented
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 & Country Club, or maybe tennis at the College or paddle tennis at Worton Park. Learn to sculpt with RiverArts before dancing the night away at the Fish Whistle, 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 renowned 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 Winterfest 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 first hand!
About Kent County...
lifestyle typical of Eastern Shore resort locations. Exclusive to Tolchester residents is its community beach, boat ramp and a multitude of planned events. The Tolchester Community Association (TCA) kicks off every season with its annual TCA Yard sale in April. In addition, residents can look forward to the summer picnic, fall spaghetti dinner, and winter holiday fest. The Hawaiian luau party in August and pork roast in July received rave reviews!
As for Tolchester Beach, it's still here! Better known as The Shanty, this lively spot serves as an entertainment destination for locals and those who boat in on the Bay. Tolchester is centrally located between Chestertown, Rock Hall & Betterton.