This collection includes materials pertaining to Tapping Reeve, James Gould, the Litchfield Law School, and alumni of the school.  It was assembled by the Historical Society over a period of years.  Many of the law books used by Reeve and his students are also held by the Society and can be found through the book catalog.  The Society's institutional records document the history of the Tapping Reeve House and Litchfield Law School building.

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.