After crossing the Chesapeake Bay on the Chesapeake Bay Bridge, US 50/US 301 head onto the Eastern Shore on Kent Island in Queen Anne's County. An eastbound all-electronic toll gantry is located past the bridge. The road continues east as the Blue Star Memorial Highway, a six-lane freeway, and maintenance returns to the Maryland State Highway Administration. The freeway comes to a diamond interchange with MD 8 and heads to the south of Stevensville through business areas, with MD 835A parallel to the south. The route reaches an eastbound RIRO intersection with Thompson Creek Road and a westbound RIRO intersection with Duke Street. From here, US 50/US 301 head east across Cox Creek and run between businesses to the north and residential areas to the south in Chester, with a westbound exit and entrance with the US50QC frontage road providing access to the businesses. The highway comes to an eastbound RIRO intersection with Cox Neck Road and a westbound RIRO intersection with Castle Marina Road (MD 18H), the latter of which provides access to MD 18 to the north. The road continues through commercial areas and passes under MD 18 before it comes to an eastbound RIRO intersection with the northern terminus of MD 552 and a westbound RIRO intersection with Chester Station Road (MD 552A), with Chester Station Road providing a connection to Piney Creek Road. The freeway runs between woods and marshes to the north and businesses to the south prior to an eastbound RIRO intersection with South Piney Road and a westbound RIRO intersection with Piney Creek Road. The route passes near more development and comes to an eastbound RIRO intersection with Dundee Avenue before a bridge over Piney Creek. US 50/US 301 reaches an interchange with MD 18, with access to and from the westbound lanes provided by Piney Narrows Road. Following this interchange, the freeway heads across the Kent Narrows on the Kent Narrows Bridge, with MD 18 parallel to the south.