During the conflict, Litchfield was considered a safe place to send important prisoners of war. Its gaol [jail] was notorious. The building no longer stands, but George C. Woodruff's map shows its former location on what is now East Street. The lines are faint, as he used a lighter color ink for buildings and roads that had already been removed.

Map showing Gaol George C. Woodruff, 1845

William Franklin, Royal Governor of New Jersey and son of Revolutionary hero Benjamin Franklin, was sent to the Litchfield Gaol after abusing his parole. He wrote, "They hurried me away about 40 Miles to Litchfield, where I was thrown into a most noisome filthy Room of I believe, the very worst Gaol in America." Franklin went on to describe his surroundings, "In this Dungeon, for I can call it no other, it having often been appropriated to condemn'd Criminals, I was closely confined for about eight Months, overrun and molested with the many kinds of Vermin, debarred of Pen, Ink, and Paper and of all Conversation with every Person, except now and then, a few Words with the Sheriff, Gaoler, or Centries. In short I was in a manner excluded human Society, having little more connexion with Mankind than if I had been buried alive. My Victuals was generally pok'd thro' a Hole in the Door, and my servants but seldom permitted to come into the Room, and then only for a few Minutes in the Presence of the Goaler and the Guard."
William Franklin to Lord George Germaine, November 10, 1778
The National Archives, United Kingdom

Officials were often given liberal parole to wander freely around the villages which held them. Major Moses Seymour was given the following orders pertaining to David Matthews, Royal Mayor of New York city and conspirator to kidnapp General Washington, "…you are directed and required to take him under your Care and him safely convey from Hartford in Hartford county to Litchfield ___ aforesaid and him there hold and keep in safe Custody permitting him only to walk abroad for the Benefit of the Air in the Day Time and to attend Divine Service at some place of public worship and that under your law or that of some other trusty keeper on the Sabbath Day, until you secure further Orders from me or from the Provincial Convention of the State of New York."
Litchfield Historical Society, Woodruff Collection, Governor Jonathan Trumbull to Major Moses Seymour, August 22, 1776

Moses Seymour House

Before further orders could be given, Seymour escaped. Loyalists in Litchfield were not limited to prisoners. Many local Anglicans remained loyal to the King, who was also the head of

their church. Matthews later acknowledged the assistance of a local man, Joel Stone, in his escape. "I found...that from the confidence placed in him he would be a proper person to assist me in making my escape to New York which he readily undertook and carried me through the country at a very great risque of his life and property."
Great Britain, Public Record Office, Treasury, Class I, Volume 634, folio I95.

Joel Stone attempted to Litchfield after the war to collect debts owed to him from before the conflict. He was unsuccessful in this endeavor, and was forced to flee the area. Eventually he went to Ontario, Canada, where he founded the town of Gananoque. Timothy J. Compeau, Curator and Public Historian for the town, authored the Web site An American Refugee: Joel Stone, United Empire Loyalist where visitors may learn more about this former Litchfield resident.