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 Although today the Winston-Dillard-Willis Creek area is often regarded as a single entity, the Umpqua River separates Winston from Dillard and Dillard from Willis Creek. Therefore, before 1900 the three communities developed independently. Winston dominates the area now, but its prominence is a new phenomenon. In the nineteenth century it was Dillard that was a growing small town, while Winston, then known as Civil Bend or Coos Junction, was nearly undeveloped. Its only notable feature was a fairgrounds that housed a racetrack. According to local legend, because of the crowd’s raucous behavior at the track, the area was called Civil Bend as a sarcastic gibe.

The early history of the entire area, then, centers on Dillard. One of the first settlers, the Reverend John Dillard, arrived in 1851 and bought the valley for $800.00. In 1854 he established the first Presbyterian Church in Douglas County at the foot of Bragg Mountain.

The town developed slowly, in part because it lies almost entirely in the floodplain. Severe winter flooding was an annual event. In 1880 the first store was opened, but real growth began in 1883 with the completion of the Oregon and California Railroad as far south as Glendale, Oregon. That same year the first train arrived at the Dillard Depot. Within two years a hotel was built, a blacksmith shop was opened, and the Dillard Post Office was established. In 1895 Mr. and Mrs. George Leonard opened Dillard’s second store.