Military Square abutted Main Street near the intersection of present-day Pleasant Street, where the municipal library now stands. This part of town earned its name from the nearby military barracks that were built in the 1840s; the square served as parade grounds for troops dispatched during the Aroostook War and for later veterans.

The first three buildings in the image were all part of the G. H. Page store. Page was in the grocery business according to the census of 1910. The fourth building is H. A. Sawyer Jewelry Store (the Sawyer family was from Ashland). The fifth building was a rented office used by a lawyer.