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This collection is comprised of valentines ranging designed and printed 1904 to 1918. Many of them have names written on them, and seem to have been given from students to teachers. Height, size, and style varies. Many of them have moveable parts, lace, macramé, and tissue paper. They are very delicate objects and fall apart easily. The valentines are styled as flat calling cards, double folio cards (some standing with a leg and some just open), while the majority of the collection are pop-ups, both with moveable and non-movable parts. A single valentine is in German, but the rest of the collection is in English.

The Robert S. Arnold Architectural Collection consists of architectural plans, site surveys, perspective sketches, contracts, and job schedules. The collection contains materials relating to the Highland Park Library, The Moraine Hotel, and several prominent Highland Park residents. Homes, buildings, and churches from the Chicagoland area can also be found in the collection including Kelly's Day Camp in Wheeling, Illinois, St. Martins Church of Christ in Chicago, Illinois, and the Serbian Orthodox Monastery in Libertyville, Illinois. The collection also contains items relating to homes built outside the Chicagoland region, including those built in Troy, Alabama. This collection contains the exhibit plans for Arnold's submission for the Chicago Tribune's Chicagoland Prize Homes Exhibition. The collection originally contained 369 rolls. The collection still contains many of the rolls relating to Highland Park, Illinois. A large collection of rolls relating to Chicago, Illinois; Glencoe, Illinois; Wilmette, Illinois, and several other North Shore communities are missing. Seven rolls were deaccessioned to the Lake Forest Lake Bluff Historical Society in 2006. One roll was deaccessioned during 2010 processing as it did not fit in The Highland Park Historical Society's collection policy. It is unclear where the other rolls are located.

Ida Pasquesi in front of house. Santi Pasquesi and Maria Sassarossi Pasquesi by garage and Luigi Pasquesi and Ida Pasquesi next Frank Sassarossi (in white t-shirt) trees next to dwelling. In front of house, Frank Pasquesi, Larry Sassarossi, Maria Sassarossi Pasquesi, Carolina Pasquesi Sassarosi, Ida (side view).

This collection contains photographs, yearbooks, report cards, attendance records, graduation and school performance programs, a financial record book, newspaper articles, and other school related ephemera from Highland Park Schools. The Highland Park Schools Collection appears to have been created at the Highland Park Historical Society and provenance is mixed and mostly undocumented. It should also be noted that many of the photographs within the collection were taken by the Brand Studio of Highland Park, IL. The following is an overview of materials that may be of special interest: Box 1 contains photographs of Highland Park School buildings and students from 1900-1950; Box 2 contains photographs of Highland Park High School sports teams and band from 1920-1950; autographed photograph of Harry E. Bolle, H.P.H.S band director; Box 3 contains school attendance and scholarship records from 1922-1941; Box 4 contains a financial record book from 1913-1923 with special mention given to information regarding the Nixon Fund on the first page; Box 5 contains materials from Highland Park Schools and related organizations such as the Board of Education for District 108 and 107. Items of special interest include: Board of Education and District 108 materials from 1909-1992; Elm Place School Building Dedication materials from 1870-1998; Elm Place School Girl Patrol materials from 1930-1984; Elm Place School plays, concerts, and award ceremonies programs from 1922-1984; publications from Highland Park Schools including Sparks, The Crier, The Green Elm and student publications from 1860-1946, 2 copies of A History of Elm Place School and Green Bay Road School (1944) by Etta Grunewald; Elm Place School graduation programs, photographs from 1893-1999; a scrapbook of photographs and written work on Elm Place School from 1916; a copy of the Blue and White, Deerfield-Shields High School newspaper from June 3, 1924; A Survey That Looks Ahead Ten Years by R.L. Sandwick from November 20, 1940; early Elm Place School photographs and documents from 1880-1984; Northwood Junior High Commencement Program from June 15, 1978; Indian Trail School photographs and documents from 1969-1990; Oak Park Terrace School photographs and documents from 1918-1990; Red Oak Junior High School Graduation Program from 1967; Red Oak Junior High “Oakies” Pendent; West Ridge School photographs and documents from 1914-1939; Braeside School documents and photographs from 1943-1957; History of Braeside School by Byron Klorfine; newspaper article about Francis Stupey Log Cabin and Braeside School from 1943; Ravinia School photographs and documents ca. 1950; miscellaneous school pictures from 1916-1930; class autograph book from 1930; scrapbook of Deerfield-Shields Township High School from 1918-1940; Lincoln School Yearbooks 1939-40; book of newspaper clippings from 1920-1950; North Shores Series and other music performance programs from 1929-1941 (includes performance by Marian Anderson, Ezio Pinza, and Fritz Kreisler); issues of Ravinia School Scribbler Newspaper, Vol. 3 No. 1 and 2 from 1931 and 1932; Highland Park

Young woman's scrapbook detailing activities and friends, including correspondence, dance cards and items from sports events at Fort Sheridan and Notre Dame college.

Scrapbook of professional photographs of Highland Park home interior and exterior in Central and Laurel Avenues area. Images on the interior wall include a young man in a Northwestern Military Academy Uniform, pendants for the academy and the University of Michigan and hunting ephemera.

High school scrapbook with images, captions, descriptions and clippings. Subjects and people documented include classes, school activities, dances (including partners), friends and teachers.

The collection consists of video productions that document the activity of the Highland Park Senior TV Production Team from 1989-1999. It contains oral histories of Highland Park seniors as interviewed by senior producers. The personal narratives include eyewitness accounts of World War II, the Korean War, the Vietnam War, the Highland Park Senior Center, cultural activities in Highland Park, and Highland Park neighborhoods.

There are four series in this collection: The Way It Was, Songs You Can See, Highland Park Senior Center, and Know Your Neighbors. Original numbers and order have been retained.