John Bartlett Runey is recognized as the first settler to the Oregon area. His cabin was built in 1841.
The first post office was established in 1848 with Egbert Bennett as the first postmaster.
The main railroad line from Chicago to Minneapolis, the Chicago and North Western Railroad came through the village in 1864.
On September 4, 1881 the Village of Oregon held an election to select a village president, clerk, treasurer, justice of the peace, and constable.
In October of 1910, the Village of Oregon voted to place a levy against the taxable property of the Village to collect $200 for the support of the Free Public Library.
The Oregon business community gathered for a group photo when the World War I monument was erected in the village square in January 1920. This is the 1st WWI monument in the United States. A dedication ceremony took place later in June.
The first concrete street in Oregon was laid in “No-Man’s Land,” also called Copenhagen Street because of the large number of Danes living on the street. It is now Jefferson/County CC. In 1923, four men, Elmer Peterson, Adelbert Peterson, Chris Johnson, and Jack Johnson laid 50 feet a day, using a hand mixer.
In 1941, Village Hall at 117 Spring St. was built.
The old Water Tower gets a facelift and lights and becomes the Tin Man