The first section of MD 282 to be paved was Main Street in Warwick, which was paved as a macadam road by 1910. The remainder of the highway from Cecilton to Warwick was paved as a macadam road by 1919. The highway from Cecilton to the east end of Earleville was paved as a concrete road in 1922 and 1923. MD 282 was paved west from Earleville along Grove Neck Road west to Mount Harmon Road in 1929. The current course of MD 282 west of Earleville was originally part of MD 283. The first section of MD 283 was paved from the split from MD 282 near Earleville north to Glebe Road in 1928. MD 283 was extended west to Crystal Beach as a concrete road in two segments. The first segment was started in 1930 and completed by 1933, and the second segment was completed in 1934. In 1934, the
Maryland State Roads Commission proposed MD 282 between Cecilton and the Delaware state line be widened to . In 1945, Cecil County proposed MD 283 be extended west to the Elk River and MD 282 be extended west toward the
Sassafras River in the third year of a three-year post–
World War II road construction program. The first proposal became reality when MD 282 was reconstructed and resurfaced from Cecilton to the state line in 1949 and 1950. The second proposal was never enacted; in fact, the Grove Neck Road portion of MD 282 was transferred to county maintenance in a May 8, 1958, road transfer agreement. MD 282 instead was extended west over MD 283 to Crystal Beach. MD 282 was reconstructed from Cecilton to Earleville in 1966 and 1967. The highway was relocated at its sweeping curve in Earleville, eliminating a right-angle intersection at Peddlers Lane and a four-way intersection with Sandy Bottom Road and Grove Neck Road. The L-shaped bypassed highway at Peddlers Lane became
MD 912, and the bypassed segments at Sandy Bottom Road became
MD 282 auxiliary routes. MD 282 was reconstructed from Earleville to Crystal Beach in 1967 and 1968. The highway was relocated on either side of Glebe Road; Old Crystal Beach Road became MD 912A. MD 282 was widened from MD 213 to the Delaware state line in 1993 and from MD 213 to the west town limit of Cecilton in 1998. ==Junction list==