The square's namesake is Harold Taylor Andrews, a resident of the West End and the first Maine soldier killed during the previous war on November 30, 1917.

On Armistice Day 1919, Portland staged parades and memorials honoring those who had fought and died in the Great War.

Part of these ceremonies included a gathering which dedicated the intersection to Harold T. Andrews.

A crowd of thousands gathered to listen to speeches from mayor Carroll Chaplin and Amelia McCudden, whose son James McCudden was a well-known British flying ace killed in action during the war.

[4] In 2015, the granite and bronze memorial was re-dedicated in a ceremony involving veterans groups, city councilor Edward Suslovic, and U.S.