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This collection relates to Captain Wilson Malcom Clayton who served as a pilot in the U.S. Army Air Corps and was assigned as liaison pilot for the 909th Field Artillery Battalion of the 84th Infantry Division in Europe during World War II. He flew L-4 Piper Cubs. The collection contains a handwritten diary that documents his activities during the war.

This collection relates to Corporal Winifred Lund Caraway who served with the United States Marine Corps during World War II. This collection contains scrapbooks, letters, postcards and photographs sent and collected by Caraway throughout World War II.

Business, personal, family and military papers, correspondence, orders, bills, pictures, publications, engineering diagrams and blueprints. This collection contains the business papers of John S. Winthrop and Mrs. Susan Winthrop, including correspondence, plantation records, bills, orders, mortgages, tax information and bookkeeping records. There are also personal and family papers of the Winthrop family, including pictures of persons such as Sindey Alder and members of the Winthrop family, as well as the military papers for Captain Guy L. Winthrop. The collection contains a set of eight blueprints and designs, the business papers of Francis B. Winthrop, and a map of Burrow Hill Place.