By the 1920s, the Old Baltimore Pike was supplanted by a parallel highway to the south from Elkton to Wilmington that was chosen as the route of US 40. The first segment of the modern MD 281 was constructed as a macadam road east from US 40 (now MD 7) on Main Street to Big Elk Creek between 1930 and 1933. In 1948, the Maryland State Roads Commission, which at the time maintained the major county highways in Cecil County, reconstructed much of Red Hill Road as a gravel road in 1948 before it was to be given a hard surface.
In the 1920s, the Old Baltimore Pike was replaced by a new highway to the south from Elkton to Wilmington, which became US 40. The first section of modern MD 281 was built as a macadam road east from US 40 (now MD 7) on Main Street to Big Elk Creek between 1930 and 1933. In 1948, the Maryland State Roads Commission paved much of Red Hill Road with gravel before it was given a hard surface.