[2] Due to the outbreak of the American Civil War, Woodward postponed his plans to start a legal practice and instead enlisted for service in the Union Army.

[4] In the next month, their captain was killed at the Battle of South Mountain and Woodward was promoted to first lieutenant.

[2] After a brief recuperation, he resumed his service as an aide to General Lysander Cutler in the Overland Campaign of 1864 until the expiration of his enlistment on July 2, 1864.

Woodward ran for United States House of Representatives in 1882 and received the Democratic nomination on the first ballot of their convention.

[10] After leaving office he resumed his law practice in La Crosse, but remained active in the Democratic Party.

At the 1886 Democratic State Convention, former congressman and Union Army colonel Gabriel Bouck was largely expected to accept the party's nomination for Governor of Wisconsin, but unexpectedly sent a letter declining the nomination at the start of the convention.

Charles Jonas of Racine was considered a strong candidate for the nomination, but was damaged by an aggressive pressure campaign driven by Labor and Socialist activists from Milwaukee.

[11] Woodward was defeated in the general election as Republican Jeremiah McLain Rusk won his third term as governor.

[12] Woodward's last significant political activity was serving as chairman of the Wisconsin delegation to the 1888 Democratic National Convention.