Established by 1839, Gloucester High School became a four-year institution by 1857. In 1889, the school moved into its then new building on Dale Avenue. The Dale Avenue building was converted to Central Grammar School in 1939. The current Gloucester High School, located along the Annisquam River, near the entrance to Gloucester Harbor, was completed in 1939, with an addition in the 1970s and a new Field House wing added in the 1990s.
On June 18, 2008, the high school drew international attention as news broke that 18 students had become pregnant in the last year, over four times the previous year's reported pregnancies. Principal Joseph Sullivan claimed that some of the girls had made a pact to become pregnant together, one even seeking a homeless 24-year-old man in her pursuits to conceive. But Gloucester mayor Carolyn Kirk quickly responded that they had no confirmation of any pregnancy pact. Finally, one pregnant student, interviewed on Good Morning America, said:
There was definitely no pact ' There was a group of girls already pregnant that decided they were going to help each other to finish school and raise their kids together.
Media reactions to the event ranged from general criticism of the episode as representing a misguided adolescent shortcut to adulthood and identity, to the matter of whether statutory rape occurred. However, most early media reactions were not completely accurate because they had not received all of the necessary information until later. During the 2007–2008 school year, two staff members began to publicly advocate that the school clinic provide contraception without parental consent, largely in response to the surge in student pregnancies. This recommendation drew opposition from the board of Addison Gilbert Hospital, which sponsors the clinic. The clinic staff, a pediatrician and nurse practitioner, resigned in protest at the end of the school year. On October 8, 2008 the Gloucester School Committee granted the use of contraceptives through the Student Health Center, provided the students had parental approval. The "pregnancy pact" controversy inspired some fictional treatments. The ' episode "Babes", airing in November 2008, featured a pregnancy pact between four high-school girls, with one becoming involved with a mentally-ill homeless man to conceive. The following March, an episode of Bones, "The Salt in the Wounds", featured a high-school girls' volleyball team with many members pregnant or already having given birth. Barbara Delinsky published a book titled, 'Not My Daughter', which was inspired by events in Gloucester. On January 23, 2010, Lifetime premiered a new movie called The Pregnancy Pact, which is inspired by these events. The controversy is also the subject of a documentary, "." The film crew interviewed a number of the girls allegedly involved in the "pact", many of whom speak publicly for the first time in the movie. The documentary purports to be the only source of the true story behind the Gloucester pregnancy pact and includes interviews with the girls and their families as well as Dr. Brian Orr and nurse Kimberly Daly, who ran the health clinic at Gloucester High during the time of the controversy. It also went international with the 2010 Spanish miniseries titled, :es:El pacto |El Pacto based on the Gloucester High pact as well as a 2011 French feature film, 17 Girls, a story of "young female friendship—and naiveté" is based on the Gloucester High "pact." It is the first feature film from sisters Delphine and Muriel Coulin.