The Randolph County Old Settlers Reunion and Fall Fair was originally the Randolph and Macon Counties Old Settlers Reunion. The initial meetings to plan the first Old Settlers Reunion were held in 1887 at a street fair in Jacksonville. The planning committee consisted of W.G. Riley. Liberty Noble, Charles Noble, William Baker, Charles Baker, and Marion McCanne. An association was soon formed. The first President of the Old Settlers Association was W.G. Riley of Huntsville. He was succeeded by John D. Dameron of Cairo who served for two years. The next President of the Association was William Boney mayor at one time of Cairo who served in the capacity of the Reunion President for seventeen years. The first board consisted of W. M. Baker, Charles Baker, Liberty Noble, and Charles Noble.
The first Old Settlers Reunion was held in Jacksonville in 1888. At that time only those living in Randolph and Macon Counties prior to 1829 were registered as Old Settlers. In 1896 it was decided anyone that had lived in the counties for 60 years could be registered as Old Settlers. In the early days the Reunion Association rotated the towns the Reunion was held in. Once it was held in Moberly, once in Cairo, and twice it was held in Macon County. The most common towns to host the Reunion in its early days were Jacksonville and Huntsville. The Old Settlers Reunion was moved to Huntsville permanently in 1900. In 1910 Macon County was dropped from the name of the fair although citizens of that county could still attend. The last person to register for the Reunion from Macon County was Webb M. Ruby in 1926.
Over the years many contests and competitions were held at the fair. There were the usual baking competitions, pet shows, beauty contests, and so forth, but some competitions were not what we usually think of. In 1931, a competition was held for the family with the most girls. That year there were also contests for best looking man under 21, shortest couple (combined height), oldest car, and largest family at the fair. At one time many of the competitions we associate with other fairs were held at the Randolph County Old Settlers Reunion and Fall Fair. In 1953, there was a horse team pulling contest as well as a livestock show. At that Old Settlers there was also a tricycle race for children under six years of age. Over the years many contests have been held such as the best old fiddler, the best horse shoe pitcher, water melon eating, sack races, pole climbing, among other competitions.
The Randolph County Old Settlers Reunion and Fall Fair is perhaps the longest running event of its type in the county. This year's Reunion will be the 128th one, and as in the past many will no doubt take part in its many activites.