Born in
Tonawanda,
New York, Woolson received an
Artium Baccalaureus degree in 1860 and an
Artium Magister degree in 1863 from
Wesleyan University. Interrupting his legal education to serve in the
American Civil War, he was an assistant paymaster in the
United States Navy from 1862 to 1865 aboard the USS Housatonic (sunk by the submarine torpedo,
H.L. Hunley) and the USS Monadnock. Following the war, he relocated to
Iowa, where he
read law to enter the bar in 1866. He was in private practice in
Mt. Pleasant, Iowa from 1866 to 1891. While in practice, he served as a member of the
Iowa Senate from 1876 to 1881, and from 1885 to 1891. ==Federal judicial service==