The Woodruff Collection primarily documents the personal life and professional career of George Catlin Woodruff, who not only practiced law for several decades in Litchfield but also served as Litchfield's postmaster and held elected positions both locally and in the United States Congress.  

His law career is extensively represented in his business correspondence with clients concerning suits in progress and with other law professionals; his law school notebooks; and his own notes on pending lawsuits.  These papers document the education and routine work of a lawyer in this period, as well as the networks among lawyers in New England and their relationships with judges, courts, and other members of the judicial system. 

The collection also illuminates the central position of the postal service in the early republic through letters sent to Woodruff in his capacity as postmaster of Litchfield.  These include not only correspondence with other postmasters concerning mail schedules and misdirected letters, but also correspondence from individuals from other towns seeking information about Litchfield inhabitants, reporting suspicious activities, and asking for assistance in publicizing their own careers.

Additionally, Woodruff's extensive personal correspondence with his family sheds light on his personal life, especially in letters to and from his brothers Lewis B. Woodruff, a lawyer in New York, and Reuben M. Woodruff, a physician.  These letters record their efforts to establish and develop their careers, their travels along the east coast and the southern United States, and family and social news.  Moreover, the collection includes Woodruff's personal papers, which trace his interest in genealogical research, the history of Litchfield, and his autobiographical efforts.

The collection follows Woodruff's political career through newspaper clippings and his own handwritten records of local and national election results, as well as documents his other business ventures, including investments in railroads, canals, and banks, and his involvement in the Litchfield Mutual Fire Insurance Company.  By extension, these papers reveal political processes and economic developments during this time period.

Also present in this collection are the papers of numerous Woodruff relatives, as well as those of other prominent and lesser-known Litchfield families.  For example, the collection documents the extensive land transactions executed by Woodruff's father, Morris Woodruff, especially in partnership with Simeon Harrison; the law career of his son George M. Woodruff; and his grandson James P. Woodruff's law and political careers.    The collection also includes many personal and business papers from members of the Seymour and Wolcott families, as well as from the family of Henry E. Gates, who served as a physician during the Civil War, and from Grant Wickwire, a prosperous Litchfield farmer.