1794: A stone discovered on a hillside southwest of Fredonia above the Fall River with this date carved into it gives evidence alluding to the presence of European explorers in the area.
1857: First European settlers came to the area.
1861: Creek Indian leader Opothle Yahola led 7,000 Native Americans, and 300 slaves, who were loyal to the Union Cause from Deep Fork, south of present day Tulsa to escape conscription into the Confederate Army. They ran north through Montgomery County to Fort Row north of Fredonia in Wilson County, hoping to find the promised food and other aid from the Union Army.
1864: Wilson County boundaries were finalized by State legislature. Wilson County held its first presidential election with 26 votes cast. This was also the first year of the federal census.
1868: Fredonia Town Company was organized, the name chosen and the town was platted. Dr. J. J. Barrett erected the first building on the southwest corner of the square.
1869: A county election on June 8 selected Fredonia as the county seat. Fredonia schools were organized on July 10th.
1870: The first newspaper of Wilson County, the Wilson County Courier, was published by John J. Jennings on January 20th. The Courier noted that there were 23 completed buildings in Fredonia and that foundations for 50 more structures were laid. Frisco railroad arrived, and the first school term of three months was held.
1871: City government first meets on May 5th. The first religious building was the Congregational Church built on a lot given by the town company. When the church closed, the building became the public library. In 1969, the old building was razed and the present library is built on that same ground. in 1871. another county election on May 23rd again selected Fredonia as the county seat. Citizens of Neodesha contested the election. Wilson County Bank was incorporated on September 9th; the bank is now known as First National Bank in Fredonia.
1872: Charges of fraud in the May 1871 election were filed in the District court. Judge Gooin ruled the election invalid and directed that the county officed be removed to Neodesha. This decision was appealed to the State Supreme Court. On February 12th the town's first large fire consumed nine business structures on the west side of the square. The fire was fought by bucket brigade.
1873: Another election was held January 28th, and Fredonia was again selected as county seat.
1874: In May, the State Supreme Court upheld the District Court's decision to disqualify the May 1871 election and remove the county offices to Neodesha.
1885: On September 7th another election was held, which passed a bond issue of $30,000.00 to build a courthouse in Fredonia. That ended the county seat debate.
1888: First graduating class of Fredonia High School.
1915: The new Wilson County jail opened. It contained the sheriff's residence and the jail. This building now houses the Wilson County Historical Society.
1918: Fredonia's ambulance company is engaged in the great battle of St. Michiel in France.
1923: Between two and three thousand people heard Zack Harris, Ku Klux Klan organizer, talk on the immigration problem in the S. M. Smith cow pasture.
1925: Ben Paulen of Fredonia became governor of Kansas. Paulen began his political career more than 25 years before as a member of the Fredonia City Council.
1936: On July 18th a national record-setting temperature of 121 degrees fahrenheit was made.
1937: Fredonia's population was 4,167.
1945: The Thomas Sheedy heirs transferred title of the old Sheedy homestead, 2 miles north of the city, to the City of Fredonia to be used as an airport.
1955: The South Mound Star and Cross light structure was erected by the Fredonia Lions Club.
1963: Fredonia City Hall was torn apart by a blast which completely destroyed the interior and roof. The hot water tank was blamed.
1969: The new library, built on the grounds of the old Congregational Church, was opened to the public.
1976: the Wilson County Historical Society held their open house in the newly acquired facility on the east side of the square - the old sheriff's residence and jail.
1991: The Gold Dust Hotel Building was selected for the National Register of Historical Places, and a complaint filed with the American Civil Liberties Union threatened the continuance of the 65-year-old Christmas Pageant.
1994: Mill Dam building renovated.
1995: On March 3rd the Kansas governor Bill Graves signed a resolution stating "Highway 75 from the Oklahoma and Kansas state lines to the steps of our state's capital be so designated 'the Opothle Yahola Memorial Highway'" and certain areas in Southeact Kansas, the Verdigris, Neosho and Fall River Valleys and that of the Big and Little Sandy Creek Valleys as the "Opothle Yahola Historic Trail."
1998: On May 30th the Opothle Yahola Memorial Trail was dedicated in a ceremony at Caney. The highway signs are in place. Also happening the same year on August 24th the new US Highway 400 was opened from Wichita to the eastern edge of Fredonia, intersecting with K47. Several months later the highway was completed to Joplin, Missouri.