Richard Montgomery High School was Montgomery County's first high school. When the Board of Education established a public high school at Rockville in 1892, it allocated $300 to build an addition to the elementary school to allow room for grades 8 through 11 to meet in the same building. The first 12 graduates received their diplomas from "Rockville High School" in 1897.

Students quickly outgrew these quarters, so in 1904 the Board purchased property at the corner of East Montgomery Avenue and Monroe Street. Rockville architect T. C. Groomes designed a grand brick building, and contractor Charles Viett built it for $20,300. "Montgomery County High School" opened in September 1905. Students came from all over the County, many traveling on the B&O Railroad from Boyds, Dickerson, Barnesville, Kensington, and other towns.

By 1910, the high school was so overcrowded that rooms for classes were rented at the Corcoran Hotel. The school was enlarged in 1916-17 to 19 classrooms designed for about 800 students, plus a room for the School Board office. During WW I, the assembly room was used as a gymnasium, with Rockville citizens donating funds to purchase equipment. The Sentinel reported that "physical culture is now admittedly so essential to perfect physical development that every community center with modern ideas recognizes this. The Rockville High School is becoming more and more a modern community center."

In 1927, the student council was organized and the first yearbook, "The Rocket", published. Art and music classes became permanent curricula fixtures in the 1930s. With the opening of a new gym in 1929, basketball became popular. The 1937 girls team was nicknamed the "Rockettes" and compared to those on the New York stage. The name, later shortened to "Rockets," is now used by all RMHS teams.

When "Rockville Colored High School" opened in 1935 at Lincoln School in Lincoln Park, the School Board officially renamed the school for white students "Richard Montgomery High School." Five years later, a fire destroyed the old building. The board purchased land near the old Rockville Fairgrounds, adjacent to the new Park Street Elementary School, and in 1942 students paraded from Monroe Street to their new school at the current site.

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