Chester, MD

Located on Kent Island right across the Chesapeake Bay Bridge, Chester is the first community you hit when arriving on Maryland's Eastern Shore. With around 5,000 residents, it offers a relaxed, small-town atmosphere that appeals to anyone looking for coastal living within commuting distance of Annapolis, Baltimore, and Washington. It shares the island with neighboring Stevensville, and both towns retain deep ties to the region's classic waterman heritage and seafood traditions.

Life here revolves around the water. You will find great spots for kayaking, walking trails and scenic bay views at Ferry Point Park, and plenty of dockside crab shacks serving the daily catch. Between local events like Kent Island Day and a friendly, tight-knit feel, Chester provides a peaceful island lifestyle paired with easy access to shopping, dining, and mainland highways.