Winsted is a census-designated place in Litchfield County, CT, that has a population of approximately 6.500 residents. Instances of prostitution and sex trafficking are not known to be widespread problems within the city, but have occurred in surrounding areas within the county. For example, in 1999, a Litchfield County man was convicted for promoting prostitution, conspiracy to promote prostitution, and racketeering. The offender also had a history of prostitution charges dating back to 1992. As a result of the investigation, the offender was sentenced to 20 years in prison and was found guilty of operation a multi-mullion dollar prostitution ring in Connecticut, New York, and Massachusetts.

Consumer level demand provides the revenue stream for all prostitution and sex trafficking, and has therefore been targeted by local law enforcement agencies as a strategy for prevention and response. Sex buyer employment loss and identity disclosure are consequences of buying sex that have occurred in the city. For example, in May, 2004, a Northwestern Regional High School teacher was suspended after reporting to police that a known prostituted person had stolen his vehicle. The sex buyer, having admitted to engaging in commercial sex, was arrested on charges of patronizing prostitution. The offender also confessed to engaging in commercial sex on numerous prior occasions from 2002 to 2004. The sex buyer had been a teacher at the high school for 27 years and was immediately placed on administrative leave as a result of his arrest. In June, 2004 the teacher resigned from his position and was no longer employed by the school district.