The state highway runs 2.57 miles (4.14 km) from MD 675 near Princess Anne north to U.S. Route 13 (US 13) near Eden in northern Somerset County.

The state highway was designated from Princess Anne through Allen to Fruitland in Wicomico County when US 13 was relocated in the early 1930s.

MD 529 was removed from the state highway system in segments north of its present terminus in sections in the late 1950s and early 1960s.

The new highway began at MD 529's present southern terminus and paralleled the Pennsylvania Railroad until curving north to intersect Allen Road west of Fruitland.

[9][7] MD 663 was assigned to the old alignment of US 13 from the junction of the 1933 and 1939 relocations south of Fruitland north along Camden Avenue to Main Street in downtown Salisbury.