Queen Anne's County made the first improvements along what is now MD 544 by 1915, when the county constructed with state aid an L-shaped shell macadam road along part of what is now MD 290 north to Crumpton and on the Fingerboard Road from modern MD 290 east to Perry Lynch Road. The first Maryland State Roads Commission–directed improvement was construction of a concrete road on the Unicorn Mills Road from MD 313 at the hamlet of Unicorn straight west to Lindsay Road in 1932. By 1933, the county-maintained shell macadam road on the Fingerboard Road near Crumpton had been extended east to Lindsay Road. The state started work from MD 290 west part of the way toward McGinnes Corner in 1934, and the macadam road was completed to west of Pearl Creek in 1935. The macadam road was extended west to McGinnes Corner by 1938.