Riddle is a city in Douglas County, Oregon, United States. The population was 1,185 at the 2010 census.

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

J. B. Riddle purchased a land claim from J.Q.C. VanDenbosch at the age of nineteen in the year 1863. In 1869, Riddle sold 140.5 acres of his allegation to his brother, Abner. When the railroad came through, it passed in the midst of the brothers’ properties. J.B. took advantage of the opportunity afforded by the railroad and untouched his profession to event from farming. He and his second wife, Mary Catching, built a hotel in what would become the city of Riddle, where J.B. opened several little eating houses to Medford, Oregon along the tracks.

As of the 2010 census, there were 1,185 people, 460 households, and 307 families residing in the city. The population density was 1,881.0 inhabitants per square mile (726.3/km). There were 491 housing units at an average density of 779.4 per square mile (300.9/km²). The racial makeup of the city was 89.7% White, 0.3% African American, 3.0% Native American, 0.5% Asian, 0.1% Pacific Islander, 1.2% from other races, and 5.2% from two or more races. Hispanic or Latino of any race were 5.1% of the population.