Artist Winslow Homer created many artworks in his New York City studio that highlighted the charm of rural life and outdoor experiences. Crossing the Pasture is one of the largest canvases he painted related to this theme.

The focal point of the work is two young boys standing next to one another in the center of the painting. Both boys are looking to the left at something in the distance. The older, taller boy stands on the left with all of his weight on his rigid left leg; his right leg slightly bent. He wears a light-brown hat with a back flap that covers his ears; a light-brown jacket buttoned up to his neck; and light-brown pants with dark brown waders up to his knees. His right arm is bent, and he grips a long stick that rests on his right shoulder and reaches back behind him. His left hand hangs by his side and holds a silver pail. To his right is a younger boy who stands a little behind him. The younger boy is much smaller―the top of his head reaches the older boy's chest. He wears a dark cap; a white, long-sleeved shirt with brown suspenders; and dark pants that are rolled up just below his knees revealing his bare feet. His right arm is behind the older boy, and he is reaching his left arm across his body to help hold the pail.

A lush landscape surrounds the boys. Dark green hills crisscross the background, and a partly cloudy sky appears at the top of the canvas. A bright blue sky and white clouds starkly contrast against the darker greens below it. A tree with a stone wall and a bull are in the distance on the left. On the far right side sits a small cottage with a cow in the field. At the bottom of the canvas, Homer used short dashes and dabs of different greens, whites, and muted yellows to create the grass and wildflowers.