The Cumberland County Court House houses a district court and a superior court. Lawyer Harriet P. Henry became Maine's first woman judge in 1973, serving in the District Court until 1990. Five of Maine's 22 Superior Court judges were women, as of early 2015, two of whom sat on Cumberland County’s bench in Portland. Eleven of Maine's 43 District Court judges (including "active retired") at the same time were women, one of whom sat on Cumberland County's bench in Portland. Only one woman out of the seven justices, Caroline Glassman, who was appointed in 1983, sat on the Maine Supreme Judicial Court bench in Augusta until her retirement in 1997, when Justice Leigh Saufley was appointed. Justice Saufley, in 2001, was the first woman appointed as Chief Justice of the Maine Supreme Judicial Court.
As of 2014, Stephanie Anderson has been elected six consecutive times as District Attorney for Cumberland County, first taking office in January, 1991, the first woman to serve in that office here or in any county in Maine. She also established Project Exodus, Maine's first Drug Treatment Court and Maine's first Domestic Violence Prosecution Unit.