The facility, controlled by the Connecticut state government, historically held inmates convicted of minor offenses, and it had a capacity of 120 prisoners. The first portion of the building was constructed in 1812 with subsequent additions in 1846 and 1890. The jail was originally operated by Litchfield County when Litchfield was the county seat of government. After 1960, when Connecticut dissolved county governance, the jail property was absorbed and operated by the State of Connecticut.

The prison held British people during the War of 1812. In the early 20th century an addition was built joining Litchfield Jail to the First National Bank of Litchfield, an 1816 structure.

In a period before the 1990s the state began allowing many prisoners into the facility, and it reached capacity. A prisoner escaped the prison, stabbed a guard, and held a man from the State of New York as a hostage, so the state government removed the violent prisoners and made it a drug treatment center for male inmates in 1992. The prisoner capacity was reduced to 30. Governor of Connecticut Lowell P. Weicker Jr. ordered the facility closed for financial reasons in 1993. [Source: Wikipedia]