The original 23 classrooms, offices, shop rooms, and cafeteria were quickly outgrown. More classrooms and a gym were added. A football field was designed within the oval of the former Fairgrounds racetrack. By the 1950s, even after grades 7 through 9 were relocated into new junior high schools, 13 more classrooms, a library, cafeteria, ballfields, and a 2,000 seat grandstand were needed. By the 1959-60 school year, the staff had grown to 105 and the student body, including 8 black students, had swelled to 600.

A major addition in 1963-64 became the front of the building, for administrative offices. In the 1980s, the A. May Nicewarner Auditorium and other rooms were added.

Since the beginning, Richard Montgomery has operated as a comprehensive high school, reflecting the varied interests and needs of the community. Manual training classes have evolved into the vocational curriculum, the academic program has been augmented with Advanced Placement and International Baccalaureate options, and a large ESOL program was added to meet the changing needs of Rockville families. RMHS music and art departments, sports teams, and student leadership training continue to maintain high standards and to provide opportunities for the young people of Rockville.

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