| State: | MD |
| Type: | MD |
| Route: | 257 |
| Alternate Name: | Rock Point Road |
| Map Custom: | yes |
| Map Notes: | Map of Southern Maryland with MD 257 highlighted in red |
| Length Mi: | 9.75 |
| Length Round: | 2 |
| Established: | 1959 |
| Tourist: | Religious Freedom Byway |
| Direction A: | South |
| Terminus A: | near Rock Point |
| Direction B: | North |
| Terminus B: | in Newburg |
| Counties: | Charles |
| Previous Type: | MD |
| Previous Route: | 256 |
| Next Type: | MD |
| Next Route: | 258 |
Maryland Route 257 (MD 257) is a state highway in the U.S. state of Maryland. Known as Rock Point Road, the state highway runs 9.75miles from MD 254 near Rock Point north to U.S. Route 301 (US 301) in Newburg. MD 257 serves the Cobb Neck of southern Charles County between the Potomac River and Wicomico River, connecting the communities of Cobb Island, Issue, Tompkinsville, and Wayside with US 301. The state highway was originally the southernmost section of MD 3, which was constructed on the peninsula in the 1910s. The portion of MD 3 south of US 301 was rebuilt and renumbered as MD 257 in the 1950s. The southern terminus of the route was cut back from Rock Point to its current location in the 1980s.
MD 257 begins at an intersection with the northern end of MD 254 (Cobb Island Road) near Rock Point. Rock Point Road continues southeast as a county highway to the namesake promontory at the confluence of the Wicomico River and Potomac River. 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. The state highway next passes through Tompkinsville, where the highway passes the southern end of Mount Victoria Road, which serves the village of Mount Victoria. MD 257 next passes through Wayside, where the highway crosses Piccowaxen Creek and intersects Morgantown Road, which leads to the Potomac River community of Morgantown. The state highway continues northwest to Newburg, where the highway meets the north end of Mount Victoria Road. 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.
Rock Point Road was the southernmost segment of the highway from Rock Point to Waldorf that was marked for improvement by the Maryland State Roads Commission in 1909. That highway was designated MD 3 in 1927. The Cobb Neck portion of the state road was constructed as a 14feet gravel road between Wayside and Tompkinsville in 1913 and a 10feet concrete road from Tompkinsville to Rock Point in 1914. The highway was completed when the state road north of Wayside was built as a gravel road by 1919. 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. MD 3 was renumbered as MD 257 in 1959. MD 257 achieved its current length when the highway between MD 254 and Rock Point was transferred to Charles County around 1989.