Maryland Route 258 is a state highway in the U.S. state of Maryland. Known as Bay Front Road, the route runs 7.13 miles (11.47 km) from Wrighton Road in Bristol east to MD 256 in Deale. MD 258 is the main connection between MD 4 and the southern Anne Arundel County bayside communities of Deale and Shady Side. MD 258 was constructed from MD 2 at Tracys Landing west to Bristol in the late 1920s and early 1930s. The highway was rebuilt at its western end and extended east from MD 2 to MD 256 in the early 1960s.

Maryland Route 256 is a state highway in the U.S. state of Maryland. The highway runs 5.28 miles (8.50 km) from MD 2 at Tracys Landing east to MD 468 in Shady Side. MD 256 connects the aforementioned communities with Deale on the shore of Herring Bay in southern Anne Arundel County. The highway was constructed at either end in the mid-1920s and completed through Deale in the early 1930s.