The state highway was originally the southernmost section of MD 3, which was constructed on the peninsula in the 1910s.

The southern terminus of the route was cut back from Rock Point to its current location in the 1980s.

MD 257 heads northwest as a two-lane undivided road, passing through the hamlet of Issue, where Swan Point Road splits to the west toward the golf course-centered community of Swan Point.

MD 257 curves to the west and crosses over CSX's Pope's Creek Subdivision railroad line, whose southern terminus is at the nearby Morgantown Generating Station, before reaching a directional crossover intersection with US 301 (Robert Crain Highway) a short distance north of the Governor Harry W. Nice Memorial Bridge over the Potomac River.

[6][7] MD 3 was widened and rebuilt with a bituminous concrete surface from Newburg to Tompkinsville in 1950 and from there to Rock Point in 1951.