Ottway, as an educational institution, was started circa 1871. It started out as Ruhamey School. In approximately 1892 a new school was built to replace Ruhamey and expand the education in the area. Ottway College was formed with the help of the teachers at Ruhamey and the local community. It remained that until 1901. The county took over then and Ottway became an elementary school until circa 1927. Ottway College was a three story structure with a dormitory. A horse barn was across the road in front of the school. Many boarded at the school. There was no student transportation as there is today. Those within walking distance walked, and the rest road horses to school. The Odd Fellows used the top floor of the school as a meeting area. The old gym had an attic that was used by the Odd Fellows as a meeting place after the original Ottway College was replaced. There used to be some very wild stories told by the students who supposedly had snuck up to the attic as to what was up there. The story was that there was a coffin and many other things that kept most of the kids from even wanting to explore. The story was true. There were two coffins in the upstairs room used by the Odd Fellows, an adult coffin and a child's coffin.
The first principal of Ottway High School was Ed Norton. When it became Ottway High School, the original Ottway College was turned around, moved back from the road and converted to a gym. A new building was built for the school. It remained this way until approximately 1943, when the old gym was torn down. Lumber from it was used for framing and sub flooring in the gymnasium that remained in use until 1998. The rest of the materials for the gym were furnished by the community with a saw mill being setup at the site and logs brought in by everyone. The WPA did the construction of the gym. The new gym was heated by a steam engine and radiators installed by Glennon Brown and Howard West.
Ottway had the first major fair in Greene County. It was held every fall on the school grounds. They always had the best carnival and midway available. Tragedy struck once in 1947 when a trapeze artist performing on a 95 foot high pole, set up in the ball field, fell to his death from the 65 foot level. Thousands of people would attend the fair. Cars would be parked on both sides of the road for a mile or more in either direction. The revenue from the fair went to Ottway School. The largest single improvement generated by the fair revenue was a cafeteria furnished with the best appliances of the time. The last Ottway fair was in 1956. The state transferred the aid it was getting to the Greene County 4-H Fair, which became the Greene County Fair.
Recent history Ottway begins in 1998 when the new gymnasium and classroom annex was built to replace the old gym that dated back to the 1940’s. This annex served the school well until the 2003-2004 school year. With growing concerns of the structural integrity of the oldest part of the school, which dated back to the 1930’s, the county decided that it would be most beneficial to tear down that section of the school and build a new addition. In late spring 2004, the oldest section of Ottway was demolished and construction on the new wing began. Students at Ottway finished the semester at what is now Chuckey-Doak Middle School and returned to Ottway in the fall semester. All of the students attended class in the intermediate section of the building, which dates back to 1961, and in three mobile classrooms until construction of the new addition was completed in late December, 2004. The addition includes eleven classrooms, a library, two bathrooms, and a teacher workroom.