MD 254 connects the mainland to Cobb Island, which was originally established as a summer resort in the early 1920s, at the southern end of Charles County.

The state highway passes between marinas and curves northwest to parallel the coast.

[1][2] The original bridge from the mainland to Cobb Island, a "noisy one-way wooden bridge that was prone to summer traffic jams," was constructed in 1923 shortly after the establishment of the island as a summer resort by Robert Crain.

[8] MD 254 had originally been assigned to Davidsonville Road between Davidsonville and Edgewater in central Anne Arundel County; that highway was renumbered as an eastward extension of MD 214 (Central Avenue) by 1939.

The new Cobb Island Bridge, which includes wider travel lanes, a sidewalk, and lighting, cost $18 million to build and opened to traffic on April 28, 2020.