Must-Sees: Kent County’s county seat, Chestertown, was voted “The Best Small Town in Maryland to Chill Out” by WorldAtlas, and it lives up to that title by offering plenty of things to do in a cozy, small-town setting. From independent shops on Main Street to art galleries in the Arts and Entertainment District, there’s plenty to do throughout the year in Washington College’s resident college town. The area may be most well-known for its annual events, though, such as the Chestertown Tea Party Festival, which includes a historical reenactment of the eponymous protest against the British government, and the Sultana Downrigging Weekend Tall Ship and Wooden Boat Festival.
The area also has several wineries that produce their own wines and cheeses, from cozy shops to fields of grape vines. Check out Chester River Wine & Cheese Co. or Casa Carmen Wines to sample spirits right in the middle of Chestertown, or make the trip to Cascia Vineyards & Winery or Love Point Vineyards & Winery to enjoy a more rural atmosphere with your wine.
Local Nature: Kent County is very rural, so nature is everywhere. The best place to go to be surrounded by it is Eastern Neck National Wildlife Refuge, a small island in Chesapeake Bay that serves as a waterfowl habitat. There are seven different trails for walking, hiking and biking, and fishing and hunting are also allowed in certain designated areas. Nearby Rock Hall also has a beach for swimming in the bay.
Another noteworthy beach is Betterton Beach, which is located on the opposite side of the county. Betterton was once a thriving resort town, but Ocean City took much of its tourism. It’s still a nice, quiet spot for fishing and swimming, especially on weekdays when there aren’t many visitors.
