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The first Highland Park High School classes were held at Elm Place School. One person graduated in the first class in 1885, Milton H. Baker, Jr. In 1887, the second floor of Brand's Paint Store on Central Ave. began to serve as the high school. Renamed Deerfield Township High in 1890, the school was called Highland Park High School colloquially until Shields Hall Opened in 1900. By 1904, the high school officially included students from Shields Township and became Deerfield-Shields High School. The 1936 opening of Lake Forest High School witnessed the return of the name Highland Park High School as Shields Township students began to attend Lake Forest High School.
The current Deerfield High School opened the late 1950s.

The Highland Park and first area schools were built in 1856, the earliest known then as Port Clinton School. In 1893 Port Clinton School was replaced by a large two-story brick building which is known as Elm Place School. During 1869 to 1961 the local school system of Highland Park continued to grow as a result of academic innovation and an involved community, and in 2011 there were eleven schools in the North Shore School District 112 of Highland Park, Illinois. These schools are Elm Place School, Ravinia School, Lincoln School, Oak Terrace School, Braeside School, Edgewood School, Indian Trail School, Red Oak School, Wayne Thomas School, Northwood School, and Sherwood School. There is also Highland Park High School which is in District 113.