History says Greenup had a school building in 1840. In 1855, Gershom Monohon was responsible for the building of a brick school. At this time the school was district #1, but later changed to #68.

The earliest records available show that Mark Sperry was hired to teach at Greenup on April 13, 1874. He taught seven years. Mrs. Rash Jones was also hired at the same time.

In May, 1876, a school meeting was held at the depot to vote whether to build a frame school or a two-story brick building. The two-story brick carried by 20 votes. Mattie Day was hired for $35 per month and Hallie Collins for $30 per month as teachers.

On June 10, 1876, Levi McCash had the lowest bid for the new building at a sum of $3478. It was accepted, and the building was completed by 1879. In July 1880, the Board agreed to dig a well on the premises, to be walled with a good stone wall ten inches thick. In September, D. Mitchell dug the well for $21.75.

Other teachers during the period 1876-1881 were D.W. Dorans, Nellie C. Lewis, Abbie Chrisman, W.H. Ward, Henry Tippett, Mary Carr, Louisa Tippett, Mary Watkins, William Trent, and Minnie Franklin. Frank Welshimer was janitor. Board members at this time consisted of Jas. L. Ryan, N.G. James, A.K. Bosworth, L. Leggett, E.L. Meeker, and A.J. Ewart.

The building burned in 1896, being replaced by the brick, eight-classroom, two-story school that existed until the 1960's.
In August, 1908, ground was broken for a two-story annex on the south side of the school. It would accommodate 100 students. In 1927, the gymnasium was added, along with an assembly hall and classrooms on the second floor to match the old building.

The first basketball game played in the new gym was played with Montrose in 1927. Players for this game were Leo Strain, Percy Ogden, Joe Nichols, John Waldrip, Delbert Hutchison, Berlin Kline, Ed Benson, Harland Titus, Donnie Ewart, and Coach Les Ogden.

An annex was built to the southeast for a band room. Later, a cafeteria. The old school accommodated all eight grades and high school at one time.

The class of 1890 was the first high school graduating class to graduate from Greenup. Members of the class of 1890 included Jessie Haight, Myrtle Ryan, Gladys Cook, J.L. Leggett, A.R. Seaman, P.H. Conzet, Hershel Talbott, Stella Davee, and Stella Harmon. The class of 1949 was the last senior class to graduate from Greenup High School. Members of the class of '49 were Randall Coleman, Ruth Brandenburg, Ella Bridges, Eulah Brown, Charles Carpenter, Evelyn Chezem, Bill Cox, Peggy Cutright, Philip Cutright, Robert Dooley, Nina Feltner, Patricia Eubank, Lloyd Flood, Donald Freeman, Wanda Gray, Loren Grissom, Martha Havens, Erma Hardy, Burl Holsapple, Paul Igou, Kent Kingery, Evelyn Bishop, Pauline Lewis, Bill McElravy, John Nees, Robert Ozier, Jim Robey, Bill Thomas, Leroy Tipsword, Dean VanTassel, Carroll Ward, Charles Winnett, Lela Nees.

Toledo School, District #24, was located at the Cumberland County Seat, approximately in the center of the county.
In the beginning, which was around 1861, students occupied a two-story frame building located in the middle of the block south of today's Neal Tire Service. In 1881 there were four classrooms built on the original two. In 1924 the gymnasium was built. Prior to that time, the PE and sports classes had been using other buildings around town. Later, a building behind the school was built which they called the "Sheep Shed." This was used by the 7th and 8th grades, taught by Bert Birdzell. Next was the cafeteria and two classrooms above it, which made a very nice school with the elementary grades downstairs and the high school upstairs.

The first graduation to be held in Toledo was 1890. Those who graduated were Mary Shull, Ura Chapman, Bertha Hanker, Nora Bloomfield, and Ivy Connor. They had only one teacher.
In 1906 Professor McCabe and his pupils gave a performance of "The Corner Store." Admission to the four act comedy/drama was 20 cents. This play was a benefit for the school for the purpose of buying a new piano.
After consolidation the high school students went to Cumberland High and the elementary students continued in Toledo until the new grade school building was completed in 1967.

On May 8, 1948, the county voted to consolidate. The district was organized in 1949 with Theodore Cutright as president of the Board of Directors and Leroy Baker as superintendent. They were ready to name the school and decided on Cumberland Unit District. For the district number, Theodore suggested #77. He said this was Red Grange's number. Red Grange, the Galloping Ghost, played at the University of Illinois in the 1920's when Theodore attended. So, that is how our district came to be known as Cumberland Unit District #77.

The building that is now the high school was built and ready for occupancy in December, 1952, located on a 39-acre site along Route 121 between Greenup and Toledo. The estimated enrollment was 343 high school students. The gymnasium was not completed until January, 1953, allowing only one game to be played that year. On December 7, 1974, the gymnasium was dedicated to Coach William Waldrip and named Waldrip Gymnasium. He had been a basketball coach and teacher for several years in the Greenup High School.