Cummings studied at the Academie Julian, Paris; the Yale University School of Fine Art; the Art Students League; and with Philip Leslie Hale, Wayman Adams, and Robert Laurent. He entered the United States Army in 1941, and was assigned to camouflage work. A private request from an officer to execute a portrait led to a regular duty reassignment to official army artist. In this capacity he did a number of portraits of prominent military figures; he continued a specialization in portraiture following his war-time service. However, it was while in the army that with Henry Varnum Poor and Sidney Simon, he conceived the idea of creating an art school that would provide an opportunity for students to work along side established artist, in a pressure-free environment. Immediately on leaving the army, the three set to work converting a chicken farm belong to Cummings into studios and dormitories. The Skowhegan School of Painting and Sculpture was inaugurated in 1946. Cummings gave his chief energies to direction of the Skowhegan School for the rest of his life.
