MD 565 was assigned to the Trappe–Easton section in the early 1940s when US 213 was moved to a new alignment between Trappe and Peach Blossom Creek in southern Talbot County.

MD 565A was designated in the late 1950s in the southern part of Easton and extended north of the downtown area in the mid-1960s.

A short distance north of Llandaff Road near the hamlet of Llandaff a short distance south of Peach Blossom Creek, MD 565 turns sharply to the east and reaches its northern terminus at US 50 (Ocean Gateway).

After crossing Paper Mill Pond, the two-lane undivided state highway reaches its northern terminus at Lee Terrace.

The portion of Main Street south of MD 565's present southern terminus was transferred to the town of Trappe in 1999.