The first section of future MD 299 to be paved was Main Street in Warwick, which was part of a road from Cecilton to the Delaware state line paved by 1919 that was later designated MD 282.
The first section of future MD 299 to be paved was Main Street in Warwick, which was surfaced by 1910. This section was part of a road from Cecilton to the Delaware state line that was completed by 1919 and later designated MD 282.