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The collection contains photographs, class reunion books, newspaper clippings, and issues of The Shoreline.

The collection is arranged by folders, and contains the commencement program (1941), photographs of the 20th class reunion (1961), a booklet from the 45th reunion (1986), two booklets from the 50th reunion (1991), photocopies of newspaper clippings from the 40's regarding high school events, newspaper clippings (1942-1944), a photograph from the 55th reunion (1997), a photograph of the Edwin Gilroy family (1997), Gertrude Frances Sesso Intermediate School diploma from Elm Place (1937), and a Vocation Reading Course Certificate (1935), an issue of Highland Park News (1943), and issues of the High School annual newsletter, The Shoreline (1938-1942).

Chamberlin's daily agendas document his life, family and activities. Various clippings, programs and other ephemera are inserted in the volumes. Highland Park (Illinois) subjects and organizations documented include Trinity Episcopal Church (Highland Park, Ill.), the Flute and Fiddle Club, North Shore Chamber Orchestra, schools and school districts, and the Highland Park Chamber of Commerce. Other organizations and events include the inauguration of Illinois Governor James R. Thompson, the American Bicentennial, and the Chicago Bar Association. There are also 2 monthly calendars, 1978-1979.

The diary in the first year of the series begins, "still unemployed."

Chamberlin diary's also documented the weather, deaths in his personal life, as well as what he ate everyday.

Club, including YWCA clubs, or school images of Betty Lou Garling, née Benson, and her mother Carrie Benson, née Gerken, active clubwoman. At least one image appears to be a graduation image from Elm Place School.

The Hotel Moraine-on-the-Lake Collection contains correspondence, records, promotional material, photographs and items relating to the operation of the Hotel Moraine-on-the-Lake. The collection contains materials from all periods of operation, but focuses mainly on the years between 1960 and 1968 when it operated as a site for industry conventions. The collection also documents the development proposed by Bert Schwartz and the community activism of the Moraine Citizens Committee. The Highland Park Historical Society was active in the last years of the hotel's existence celebrating its history and accruing items that would become this collection. Also documented in this collection is the Hotel Moraine (Highwood, Illinois). The Hotel Moraine (Highwood) is represented by news clippings, photographs, and original architectural plans

Letters written from Lake County, Illinois soldier home to his parents in Warren Township, Illinois regarding life and events in the Illinois 65th Infantry regiment and on the battlefield. Correspondence, discharge and pension papers, and newspaper article are arranged chronologically. The folder also includes mounted uniform buttons and Army and Regimental pins and the History and Roster of the Sixty-Fifth Illinois Infantry. There are photocopies of all the documents in a second folder

This collection contains images and advertisements from the Brand Brothers Studio. Images range from the Brand family at various events to other local families and even individual people. All advertisements for this collection are for the Brand Brothers Studio and range from calling cards to calendars.

This is a topical file, arranged alphabetically by subject. Subjects include people, places, buildings and events in Highland Park, Illinois.

Various Highland Park and neighboring communities arranged chronologically and by decade, white and yellow pages : 1890-1999 ; 1999-2000 ; 2001 ; 2002 ; 2002-2003 ; 2004-2005 ; 2007 ; 2008-2009 ; 2009-2010 (2) ; 2010 ; 2010-2011 ; 2011-2012 (2) ; 2012 ; 2013 ; 2013-2014 ; 2014 (2).
Issues dated 1908-1913 have been digitized and are available on the Library's website via the link below.