The highway runs 11.96 miles (19.25 km) from Eastern Neck Island in the southwest corner of Kent County north to MD 21 near Tolchester Beach.

MD 445 begins as Eastern Neck Road at the north end of the bridge that connects the mainland with Eastern Neck Island, an island on the north side of the mouth of the Chester River that comprises the southernmost land in Kent County.

MD 445 heads north as a two-lane undivided road along Eastern Neck parallel to the shore of the Chesapeake Bay, along which the highway passes the historic home Trumpington.

North of Rock Hall Ball Park, the highway leaves the town and continues as Tolchester Road.

[3][4][5] The remainder of MD 445 was one of several state highways whose construction as 9-and-16-foot-wide (2.7 and 4.9 m) concrete roads was partially funded by a $900,000 Kent County bond issue in 1929.