Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. It is the principal city of the Pittsfield, Massachusetts Metropolitan Statistical Area which encompasses all of Berkshire County. The population was 44,737 at the 2010 census. Although the population has declined in recent decades, Pittsfield remains the third largest municipality in western Massachusetts, behind only Springfield and Chicopee. In 2006, Forbes ranked Pittsfield as number 61 in its list of Best Small Places for Business. In 2008, Country Home magazine ranked Pittsfield as #24 in a listing of "green cities" east of the Mississippi. In 2009, the City of Pittsfield was chosen to receive a 2009 Commonwealth Award, Massachusetts' highest award in the arts, humanities, and sciences. In 2010, the Financial Times proclaimed Pittsfield the "Brooklyn of the Berkshires" in an article covering its renaissance at that time.
In 2012, the city was listed among the 10 best places for single people to retire in the U.S. by U.S. News & World Report, due to the high number of single older residents and higher likelihood of finding companionship or a partner.
In 2017, the Arts Vibrancy Index compiled by the National Center for Arts Research ranked Pittsfield and Berkshire County as the No. 1 medium-sized community in the nation for the arts.
The Mohicans, an Algonquian people, inhabited Pittsfield and the surrounding area until the early 1700s, when the population was greatly reduced by war and disease, many migrated westward or lived quietly on the fringes of society.
In 1738, a wealthy Bostonian named Col. Jacob Wendell bought 24,000 acres (97 km2) of lands known originally as Pontoosuck, a Mohican word meaning "a field or haven for winter deer", as a speculative investment.