In 1814 Winder entered the United States Military Academy at West Point, and graduated 11th of 30 cadets in 1820.
During the early 1820s Winder went through numerous transfers going from the U.S. Rifle Regiment in 1820, to the 4th U.S. Artillery[REF] Winder resigned his commission on August 31, 1823, and would not return to the Army for almost four years [REF].