Glenwood is considered one of the oldest schools in the region.
Glenwood and the Little Red Schoolhouse was founded as a rural school district only weeks after the opening of the Cherokee Strip in 1893. The Glenwood School was annexed to the Enid Public Schools in 1964. It served the surrounding rural area during the first half of the twentieth century, first as a one teacher school, and later as a two teacher school.
The school has a colorful history. It was started in a dugout on the old Glenn farm west of Enid. It was originally located about a quarter mile west of its current site, on what was the Walter O. Beebe farm. The current A frame building, the "Little Red Schoolhouse", was constructed in 1895, and modern additions constructed in 1958, 1962 and 1964. In 1915, the building was taken apart, transported by wagon, and reassembled on its current site. After Glenwood became a part of the Enid Public Schools, a south wing was built in 1966, supplying space for upper grade classrooms and temporary central library facilities.
Mrs. Arlow Johnson, who taught at Glenwood between 1917 and 1920, said the school was considered a model at that time in domestic science and agricultural instruction, and that visitors from as far away as Denver and Chicago came to observe the instruction. Some of the early day teachers at Glenwood were Charles Evans, Cynthia Rice and O.E. James. Former pupils in the Enid area are numerous, and include Mason Hart Sr., Mrs. Oran Bland, Mrs. Gerald Alley, Floyd Jenkins, and Harvey and Nick Urban.
By 1955, Glenwood's enrollment was 49. The teachers were Frieda Driever and Olive I. Collins. 1955-56 enrollment was 44. Teachers were Miss Driever and Thelma VanBoskirk. 1956-57 enrollment was 55. The teachers were Mrs. Irene Hromas and Mrs. Leah Hogan. They continued through the 1957-58 term with 62 enrolled.
The 1958-59 enrollment was 69. Mrs. Hogan and Mrs. Hromas were joined by a third teacher, Joyce Boehnke. Those three teachers continued through the next two terms, with 75 enrolled in 1959-60 and 89 in 1960-61. In 1961-62, the enrollment increased to 92 and a fourth teacher, Sharon Smith, was added. The 1962-63, enrollment was 86. Mrs. Hromas and Mrs. Hogan continued with two new teachers, Audrey Presnall and Virgina Bergfield. The 1963-64 enrollment was 103. Janet Liberty and Gail Zink came as teachers that year. Mrs. Hromas , Mrs. Hogan and Mrs. Presnall continued at Glenwood.
The decade from 1954 to 1964 saw the Glenwood School double in size. The City of Enid was growing westward and several housing developments were opened in that area. The residents voted in 1964 to annex Glenwood School to District #57, Enid Public Schools.
Mrs. Hromas continued as principal until 1966 when she was suceeded by Mrs. Marjorie Collier. In 1966, the enrollment grew to 150, in 1967 to 195, and in 1968 to 225.
A new south wing was constructed in 1966 with a large "open school" addition added in 1979.
In 2009, Enid voters approved a 99 million dollar bond for construction, repairs and remodeling district wide for Enid Public Schools. Work began the summer of 2010 at Glenwood with the renovation of the restrooms throughout the school. Renovations also took place in the famous "Little Red Schoolhouse" portion of the school.
Glenwood currently has nearly 500 students and continues to grow and change every year.