In those two small rented rooms, Robert Kerr, the first principal and sole teacher, welcomed thirty-six young women.

Thus began the unique legacy of Western, a pioneer in women's education, along with its companion Eastern High, in the United States.

moved to a new, more expensive building specifically constructed for the girls' high school on Lafayette and McCulloh Streets in the northwestern residential neighborhood of Upton.

After several other moves, in 1928 the school moved to twin H-shaped structure of red brick and limestone trim in an English Tudor / Elizabethan /Jacobethan architecture on Gwynns Falls Parkway, opposite financier George Brown's estate "Mondawmin" which was replaced by one of the earliest enclosed malls in 1956), which was the duplicate of a similar new building for sister Eastern High in 1938 on 33rd Street and Loch Raven Boulevard.

Finally a new modern Western High finally opened in its current location at 4600 Falls Road at the northwest corner with West Cold Spring Lane (just east of the stream Jones Falls which divides the city) in September 1967, sharing a joint, huge, modern campus with the then all-male Baltimore Polytechnic Institute to the west, the city's premier mathematics/science/technology and engineering magnet public high school, previously founded 1883 on little Courtland Street as the Baltimore Manual Training School, and renamed a decade later.

The new "Poly-Western Complex", on the drawing boards for five years, was one of the most expensive and largest high school campuses constructed in America up to that time.

Western's most rigorous academic program is the "Advanced College Preparatory" Program, ("The 'A' Course"), which was established in 1933 by a joint agreement between Western and the then also all-female Goucher College (formerly located on the 2400 block of St. Paul Street in the Charles Village neighborhood in northern Baltimore City and relocated in the 1950s to the northeast of Towson, the county seat of suburban Baltimore County).

Western also annually produces championship athletic teams and prize-winning performing arts students and sponsors more than 40 different type of clubs, organizations, service groups and publications.

They won 35 or more District IX Baltimore City Championships and have been to State Finals a record 14 times (the most in Maryland history).