Riddle was founded by John Bouseman Riddle, the son of William H. Riddle, for whom the town was named. William H. Riddle was a native of Springfield, Illinois, who settled in the area in 1851. By 1881, the Southern Pacific Railroad line south of Roseburg had a station here called "Riddlesburg", which was changed to "Riddles" in 1882 and to "Riddle" in 1889. A post office at this location opened under the name of "Riddles" in 1882 and was changed to "Riddle" in 1910.
Riddle was founded by John Bouseman Riddle, the son of William H. Riddle, for whom the town was named. William H. Riddle was a native of Springfield, Illinois, who settled in the area in 1851. By 1881, the Southern Pacific Railroad line south of Roseburg had a station here called "Riddlesburg", which was changed to "Riddles" in 1882 and to "Riddle" in 1889 A post office at this location opened under the name of "Riddles" in 1882 and was changed to "Riddle" in 1910