The Brookline Riding Academy, also known as the Brookline Riding School, opened November 1, 1895 right in the Village Square. It took over the large quarters of the car house and horse stables of the West End Railway Co. which had recently switched to electrified cars. The group is shown in the small lot outside the school. Alice Sargent and Dorothy Forbes, identified here, were wealthy equestrians who helped organize, from at least 1914-1917, an annual charity event hosted at the school with contests, prizes and trophies. A trophy is noted on the seat of Sargent’s carriage and the rear of the large billboard that faced the Village Square is observed.

Sargent, never married, lived her entire life in a 40-room mansion that was part of the Sargent family compound known as “Holm Lea” in the Warren St. area of Brookline.

[Courtesy of the Digital Commonwealth (CC BY-NC-ND). From the Brookline Photograph Collection published by the Public Library of Brookline]