Pitcairn Borough built its first school house in 1896. In 1916, Pitcairn erected Pitcairn High School. Elementary students attended Pitcairn 1, 2, or 3, Elementary Schools. In 1955, the schools in Monroeville and Pitcairn merged to form the Monroeville-Pitcairn Joint School District. At that time, officials began making plans for a new senior high school. Official action was voted in February 1956, then ground breaking in January 1957. In 1960, the joint venture was renamed the Gateway Union School District, and in 1965 the name changed to - Gateway School District.

The joint School Board selected the name Gateway Senior High School. By September 1958, 900 students from Monroeville and Pitcairn were occupying the new high school. The first graduating class of 196 students received their diplomas in June 1959. For the next 25 years, grades 10-11-12 would attend school in the high school. Elementary students attended school at Jordan Elementary, Northern Pike, Garden City, Mellon Plan, Evergreen, Patton Heights, Ramsey, or Mosside Elementary Schools. 1983 marked the beginning of a new era at Gateway. Ninth grade was moved out of South and Monroeville Junior High Schools to the high school, South Junior High School became the Gateway Upper Elementary (5-6), and Monroeville Junior High School became Gateway Junior High School (7-8). Eleven years later, in 1994, Gateway Upper Elementary became the Moss Side Middle School (5-6), and Gateway Junior High School became Gateway Middle School (7-8). In 2009, the Moss Side Elementary School was renamed the Dr. Cleveland Steward, Jr. Elementary School in honor of the Superintendent. In 2011, Pitcairn Elementary School was closed.

Students in the District may attend Gateway High School for Grades 9-12 and Gateway Middle School for Grades 5-8. Depending on the location of a resident’s home and class size, students in K-4 attend one of four elementary schools: Evergreen, Dr. Cleveland Steward Jr., Ramsey, or University Park. Other options include the Gateway Cyber Academy, approved private schools for some students with special needs, a public charter or Cyber School, or any of the non-public schools located within 10 miles of the District’s borders.