Pittsfield is the largest city in Berkshire County, Massacusetts. The city has a population of roughly 44,000, and is located near the state’s western border, near Albany, New York. Prostitution and sex trafficking are well documented problems in the city.  For example, in 2017 two Massachusetts men were accused of using a residence at a senior living facility to conduct a prostitution ring. A police press release alleged the men recruited women with drug problems into prostitution and that once used his residence at a senior living facility as a place to conduct prostitution.  They allegedly facilitated meetings with male sex buyers and transported women to various locations, where they would allegedly wait nearby and take a portion of the earnings. Sometimes, they would allegedly compensate the women with drugs in lieu of cash. The drugs allegedly included heroin, cocaine and prescription medication. In 2019, one of the men was sentenced to 10-12 years in state prison after pleading guilty to multiple counts of human trafficking and acting as a pimp in the Pittsfield prostitution ring; he admitted to nine counts of human trafficking, seven counts of deriving support from prostitution, two counts of enticing a child under age 16, and single counts of rape, intimidation of a witness, conspiracy, and open and gross lewdness.

In response to complaints from the community, the Pittsfield Police Department occasionally conducts street-level reverse stings. The identities of those arrested are usually released to the public. For example, in the Fall of 2017 several alleged sex buyers were arrested and at least two men faced human trafficking charges as Pittsfield police continued to enforce prostitution and drug laws in the city. One of the sex buyers allegedly told police he had sex with several women who were heroin addicts, and paid them anywhere from $10 to $50 each. A pimp arrested in the same operation was accused of recruiting female addicts, advertising their services online, and taking them to their appointments. He allegedly kept most of the money and threatened to report the women to police if they did not continue to sell sex and surrender their proceeds to him; we was charged with four counts of human trafficking.  By December 2017, a fourth man had been arrested and charged in an ongoing investigation into a local prostitution ring. A 71 year old man was accused of paying women with cash and drugs for sex, transporting them for purposes of prostitution, having prostitutes living at his home and assisting them in obtaining drugs.  At least three other men had been arrested previously on various charges connected to the investigation, and another has been charged with paying for sex on several occasions.The identities of the men were released in news reports.