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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.

The Highland Park Public Library its doors on April 6, 1888.
Less than a year earlier, at the July 7, 1887 City Council meeting, residents had presented a petition for a public library in Highland Park. On September 14, 1887 the Highland Park City Council adopted an ordinance for the establishment of a tax-supported public library and appropriated $260 annually for its maintenance. The Library collection included 400 books and was housed at the same space the City Council rented on the first floor of the Charles A. Kuist Hardware Store on the Northside of Central. Marsalene Green served as the first librarian.
In July 1889, Library moved to the newly constructed City Hall building on Central Ave. and Green Bay. As the collection continued to grow, library moved to the former Young Men's Club House on Sheridan Road in 1900 where it remained for five years. Plans for a new library were proposed in 1903. The Highland Park Woman's Club led a fundraising campaign for the participation of Andrew Carnegie, who donated $12,000 in its construction. The A. C. Thompson family donated the land with the caveat it be used exclusively in perpetuity for a public library.
Highland Park and its public library collection continued to grow. In 1927 the board of trustees and the newly hired librarian, Cora Hendee, the library's first professionally trained librarian, proposed a new library building.
Holmes and Flinn were charged with designing the space, and chose a gothic style with limestone. The finished library was dedicated on September 20th, 1931. The first renovation to this library came in 1960, when the children's collection outgrew its space and was given a new wing on the building's west side, designed by Bertram Weber. In 1976 a modern adult wing was also added to the south side by Wendt, Cedarholm, and Tippens. A series of renovations stretched from the late 1980s to 2000, focusing on access for people with disabilities, heating, ventilation, electrical, lighting and layout redesign. Several renovations have occurred in the 21st century.