the pocomoke city–stockton road was paved within stockton and from market street east to groton road in pocomoke city by 1910. two sections of the state highway were paved from the pocomoke city end in 1915 and 1917. by 1921, sections were built from stockton west to old mill road and east to goodwill from the pocomoke city end. the highway between pocomoke city and stockton was completed in 1923. md 366 was under construction from the eastern end of pavement in stockton to george island landing by 1934 and completed in 1935.