Chester Business Directory

Chester is an unincorporated community on Kent Island in Queen Anne's County, sitting alongside Stevensville as one of the two census-designated places that together form the island's commercial core. Like Stevensville, Chester grew rapidly after the Chesapeake Bay Bridge opened in 1952 and U.S. Route 50 was converted to a freeway, turning Kent Island into a suburban gateway between the Eastern Shore and the Baltimore-Washington region. Chester is home to a substantial share of Kent Island's retail capacity, including shopping centers anchored by national chains, alongside newer mixed-use development serving the area's growing residential population. The community sits within walking and biking distance of the Cross Island Trail and is close to Kent Narrows' waterfront dining and marina district. With Kent Island serving as Queen Anne's County's primary retail hub for both year-round residents and the heavy seasonal traffic bound for Maryland and Delaware beaches, Chester functions as a key piece of that commercial base, complementing Stevensville's historic downtown with newer shopping and residential growth.