Thomas N. Bowler, sworn into office as High Sheriff of Berkshire County on January 5, 2011, is the 21st man to hold that office since the county was founded in 1761. Now the supervisor of one of the most technologically advanced county correctional facility in the Northeast, Sheriff Bowler joins a legacy of Berkshire County Sheriffs who guided the office, first from their homes, and then from county jails in Sheffield, Lenox and Pittsfield.

The first county jail was located in Sheffield in 1733. Prisoners were housed here until 1765, when Lenox became the site for the jail. In 1812, the Lenox jail was destroyed by fire, and inmates were then housed in the basement of the Superior Court building in Pittsfield.

Elijah Williams, brother of Williams College founder Col. Ephraim Williams, was the county’s first Sheriff from 1761 to 1776.

Graham A. Root of Sheffield, originally appointed Sheriff by Gov. Henry J. Gardner in 1855, was the first elected Sheriff of Berkshire County in 1857. It was during his term that the Berkshire County Jail and House of Correction was built at 264 Second Street in Pittsfield. The new jail, built of marble and pressed brick by Civil War veterans at a cost of about $190,000, accepted its first inmates in 1871.

During a time when county jails still held executions, the Second Street jail was the site of two hangings, convicted murderers John Ten Eyck in 1878 and William Coy in 1893 – the final inmates put to death in Berkshire County.

Sheriff J. Bruce McIntyre, first elected in 1933, would serve 30 years, longer than any other Berkshire County Sheriff until Sheriff Carmen C. Massimiano, Jr., who served 32 years. During his term, Sheriff McIntyre twice resisted efforts to abolish the Berkshire County Jail and House of Correction. First came an unsuccessful effort in 1935 to consolidate all Western Massachusetts jails in Springfield. Later, an effort by the Berkshire County Commissioners to close the jail and turn it into a weapons-producing factory during World War II was also thwarted.

In the 1960s, Sheriff John D. Courtney, Jr., initiated such innovations as work release and education programs, and tore down a shoe manufacturing plant that had been part of the jail, but had been unused for many years.

As a growing inmate population led to overcrowding at the Second Street jail in the 1970s, the first proposal emerged for a new Berkshire County Jail and House of Correction. The proposal was for an $8 million facility to be built on Dan Fox Drive in Pittsfield, but the proposal never made it through the legislature.

Additional medical staff and human services programs were instituted. A $2.7 million cell security system was added in 1985.

But as the inmate population and correctional needs of Berkshire County continued to outgrow the capacity of the Second Street jail, the state legislature approved funding for the new jail in 1996. A site was selected at 467 Cheshire Road in Pittsfield. The groundbreaking, attended by Gov. A. Paul Cellucci, was held Sept. 28, 1998. Construction of the new $39.1 million, 160,000-square foot, state-of-the-art facility began in March of 1999. The new jail was dedicated Jan. 5, 2001. Inmates were moved into the new jail from Second Street on Feb. 12, 2001.

In 2002, the Berkshire County Sheriff’s Office and the Pittsfield Public Schools collaborated to form the Juvenile Resource Center at the old jail on Second Street. There, at-risk students age 14 and older serve out their school suspensions by participating in an intensive education and counseling program designed to address the behavior that led to the suspension, and return the students to the school classroom.

Berkshire County Sheriffs

  • Elijah Williams, 1761-1776
  • Israel Dickson, 1776-1781
  • John Fellows (designate during Revolutionary War)
  • Caleb Hyde, 1781-1791
  • Thompson J. Skinner, 1791-1792
  • Simon Larned, 1792-1811
  • Henry C. Brown, 1811-1838
  • Thomas Twining, 1838-1843 and 1848-1852
  • Edward Ensign, 1843-1848 and 1852-1853
  • George Willis, 1853-1855
  • Graham A. Root, 1855-1881
  • Hiram B. Wellington, 1881-1887
  • John Crosby, 1887-1896
  • Charles W. Fuller, 1896-1905 (died in office)
  • John Nicholson, 1905-1932
  • J. Bruce McIntyre, 1933-1962
  • Thomas H. Sullivan (interim during World War II)
  • John D. Courtney, 1963-1978
  • James J. Mooney, 1978 (interim 3 months)
  • Carmen C. Massimiano, Jr., 1978-2011
  • Thomas N. Bowler, 2011-present