Oregon founder John Phelps arrived on the banks of the Rock River in 1833, just after the end of the Blackhawk Wars in nearby Stillman Valley.

A chance meeting with the son of Alexander Hamilton led Phelps to stake one claim, but he continued onward, choosing to settle in what is now Oregon because it was on a direct route from Galena to Chicago. Within three short years, the village had grown to include a church, school, post office, grocery store, and blacksmith's shop.

Phelps was determined to see a road built from Galena to Chicago through Oregon, and when a Galena-Chicago route was constructed through Naperville and Dixon, Phelps undertook to build his road at his own expense. The power struggle between Oregon and Dixon also extended to control of Ogle County, and when Phelps won that three year battle and Oregon was established as the seat of the newly formed county in 1837, Dixon promptly organized a petition to establish Lee County.

The history of the area is rich and varied, with Prairie Pirates and vigilante justice that resulted in the now-famous trial in which 112 men from Oregon, Sycamore, and surrounding towns were tried and acquitted for the execution of gang leader John Driscoll and his brother William.

The commencement of harness-racing at the Ogle County fair brought such distinguished-and varied--guests as Judge James Cartwright and Frank and Jesse James, who visited the Ogle County Fair with the Younger brothers just days before the Minnesota bank robbery where the Younger boys were killed.

The serene beauty of the area attracted a group of artists, led by Lorado Taft, who established the Eagle's Nest Art Colony in 1898. In the ensuing years the colony was generous to the local area. Lorado Taft created two well-known sculptures for the area: the 48-foot, concrete-reinforced "The Eternal Indian" that overlooks Lowden State Park and Taft's 1916 memorial to local veterans.

This artistic spirit endures in Oregon today, through the Arts Alliance, The Performing Arts Guild, and The Fields Project. Concerts in the Park have been an Oregon tradition for more than a century, and were originally performed on the upper level of a combination bandstand/jail.

The area retains its natural beauty as well, with three state parks and a state forest: Lowden State Park, Castle Rock State Park, Lowden-Miller State Forest and, White Pines State Park in nearby Mt. Morris.

Ogle County Historical Society