Edward Penfield (1866–1925) was born shortly after the Civil War in Brooklyn, New York. His father, Josiah, was a bookkeeper and, later, a merchant. His uncle, Henry, owned an engraving studio just a few blocks from where Josiah worked. The proximity was apparently enough to leave an impression on young Penfield. It was the artist, rather than the merchant, whom he would emulate.
The Art Students League (ASL) of New York was founded in 1875, when Penfield was just a child. The school quickly became a prominent site for blooming artists and remains one to this day. By the time Penfield reached his early 20s, he began attending classes, where he studied under the renowned artist, George de Forest Brush, who was known for his Native American art.