In 1850, a one-room school house was built on lot number 66, which was on Hubbard Street. After many years of use the one room school house became too small. In 1872 it was torn down and a new two-story building, costing three thousand dollars, was erected in its place. The school ran until it was sold in 1902. It was torn down in 1945 after it was used as a home.

The new building was erected in 1902. The building was a two-story building with four rooms. This is where grade school and high school classes attended. Mr. John W Trafzer was the first and only teacher in the high school at the time, and principal over the entire building. The County Superintendent of Schools, the Winslow School Board and Mr. Trafzer established the curriculum for a four year High School program: 4 years of English, 3 years of history, 2 years of algebra, 2 years of geometry, 1 year of advanced mathematics, 2 years of Latin, 3 years of science, and 1 year of general book-keeping.

In 1921, the Community High School District was organized. There was also an addition built to provide for an assembly hall on the second floor, two classrooms on the first floor, and a home economic room and inside toilets with running water in the basement.

In the late forties a law required the reorganization of the county into larger districts. Winslow was unable to form its own district for three reasons: One, Winslow did not have the population required. Two, the state line prevented inclusiion in a district of the Wisconsin territory long served by Winslow High School. And three, a large eastern portion of the Winslow school district chose to annex to Orangeville rather than Lena-Winslow. In June of 1949 the new Lena-Winslow Community Unit was formed.

Due to a passing of a referendum in 1956 for a single hight school, Winslow High School did not have long to live, for it closed in 1958. In 1957 a new grade school building was built east of the gymnasium. The new building had seven classrooms, each 25 by 30 feet. An additional room was added south of the gymnasium on the first floor level later on. During the summer of 1958 the old high school and grade school building was razed, leaving only the basement. The basement houses the office, two rest rooms, the heating plant, and one classroom. This past summer (2001) new windows and siding were put on the Winslow building to make it more fuel efficient and attractive.

The Winslow school building has had a long and varied history. It stands today as a tribute to the dedication and foresight of the many men and women who held and contiue to hold learning as a high ideal. At this historic 100th anniversary, it remains an integral component of the Lena-Winslow School District.

(All information obtained from The History of Winslow by Harold Fowler and the WIN-EL of 1958)