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The Highland Park Rail Road collection chiefly contains graphic materials to the history of the Chicago Northwestern Railroad (CNWRR) and the Chicago North Shore and Milwaukee Railroad (CNSMRR or CNSRR), especially in Highland Park, Illinois and neighboring depots. Ephemera found in the collection includes correspondence, train schedules, tickets, dining car menus, advertisements, maps, stock certificates, periodical clippings, reproduction station blueprints and photographic materials; including glass slide negatives. The bulk of the collection dates from from the late 19th to the early 20th century. However, the dates span circa 1850 into the 21st century.

The Highland Park Historical Society created this artificial collection from diverse donors, including Arthur Durbin, the Highland Park News, Harold G. Mason (President CNSMRR) and other railway agents.

Materials in this collection include yearbooks, minutes, announcements, scrapbooks, newspaper publications and programs. Box 1 holds the first accession: announcements, minutes, and sheet music, circa 1950-1989. It is arranged chronologically.
There are two series in the 2014 accession: records and scrapbooks.
Box 2 holds five scrapbooks assembled by members and the Club. One scrapbook contains minutes, clippings and other documents related to scholarship concert, 1956 - 1958. Other scrapbooks are chiefly composed of newspaper clippings and fliers dated 1950 -1973, 1973 - 1990, 1990 - 2006, 2007 - 2010.
Box 3, 1928-2010, holds minutes, treasury ledgers, club bylaws, newspaper drafts and clippings, and a club history:
Ledger, July 1929 - May 1981
Secretary's board meeting notebook, February 1928 - June 1938
Treasurer's notebook, May 1960 - May 1981
Treasurer's notebook, August 1981 - May 1994.

Likely created by Henry X Arenberg, this collection of Kodachrome slides documents local landmarks and civic life in Highland Park and Highwood, Illinois during the late 1960s and early 1970s. Many slides show Highland Park's downtown shopping and business district, Central Avenue, and document the area's changing landscape including the construction of medians and businesses. The slides contain images of houses, businesses, the annual July 4th parade, municipal buildings, the relocation of Highland Park Historical Society's Stupey Cabin and fire and police personnel. This collection also documents recreational activities such as camping and participation in Girl Scouts.

This collection documents the Highland Park Hospital. There are two series: Friends of Highland Park Hospital and Highland Park Hospital.

The first series holds reports and other materials created by the Friends of Highland Park Hospital and related organizations. The community funded hospital and its supporting organizations created and disseminated updates on the hospital's progress, events, and free general health information. The Hospital also had a Thrift Shop, run by the Highland Park Hospital Auxiliary. This series includes newsletters, annual reports, correspondence, pamphlets, and thrift shop information.

The second series, Highland Park Hospital, documents the Highland Park Hospital. It holds material to increase awareness and promote the Hospital. Annual reports, early birth records, correspondence, hospital development information, program information, pamphlets, newsletters, newspaper clippings, newspapers, photographs (images and negatives), and stock certificates comprise this collection.

The collection consists of photographs of Gertrude Knapmiller Ronzani, Floyd Presley, Theresa Slack, John Frantonius, Marie Knapmiller Frantonius, and John Peterson. Also included are a lady's lace cap, a booklet celebrating the 20th anniversary of the hospital in 1938, a postcard, and a photocopy of the fifteenth census of the United States of 1930, issued by the Department of Commerce - Bureau of the Census.

Class images of grammar schools St. James School, Elm Place School, Ravina School, Deerfield Grammar, Oak Terrace, Lincoln School.