While still a midshipman attending the United States Naval Academy, he was activated early for duty in the Spanish–American War,[2] during which he served on the armored cruiser USS Brooklyn.

In November of that same year, he joined the China Relief Expedition representing the United States in the Eight-Nation Alliance opposing the Boxer Rebellion uprising.

Several years later, with a second star on each shoulder, Rear Admiral (upper half) Woodward was assigned command of the U.S. Third Naval District, which covered Connecticut, New Jersey, and southern New York and had its headquarters in lower Manhattan.

(Ironically, just three years later, his son-in-law Miles Browning would prove that opinion wrong by devastating the Japanese Navy with aggressive carrier-launched aerial attacks at the Battle of Midway.)

Forcing rights of condemnation under eminent domain, the yard took over the old Wallabout Market abutting it to the east, using the expanded space to build two additional 1100-foot dry docks, a new foundry, several subassembly shops, and a materials laboratory.

Under Woodward's oversight, additional docks and berths were constructed on the East River, and miles of roads and railroad tracks were added to interconnect the upgraded facility.

In 1940, the Brooklyn Eagle carried numerous speeches of his in which Woodward warned not only of America's "third-place" status, but also that the United States Army lacked the strength to repel a potential attack on the Navy Yard if an enemy managed to break through the nation's naval defenses.

In a speech delivered on what proved to be the eve of war, 6 December 1941, Woodward predicted that the United States Navy would soon be able to defeat any and all naval forces in the world, in both the Atlantic and Pacific oceans simultaneously.

He was called back to active duty the very next day, and his words were proven prescient by his beloved Navy's successful prosecution of both the Pacific War and the Battle of the Atlantic.

His collection of papers spanning the years 1915 through 1968, which include correspondence, news clippings, publications, photographs, personal writing, and souvenirs which document his exceptionally long Navy career, are housed in the U.S. National Archives.