Circa 1930, State Highway 299 followed today's Route 341 between Route 45 and US 202.
SH 299 is an offbeat number; in the years before 1932, the state had generally used numbers in order starting at 100 (primary) and 300 (secondary). The 100's had overflowed into the 200's by that time, but only as high as about 226. The 300's had not overflowed at all. In that context, 299 is out of place.