[1] Underwood attended school in Middlesex in Rushville and took a banking course at the Rochester Business Institute, after which he began working on his father's farm in Overackers Corners.
In around 1940 he became manager of the Middlesex Corporation Association, resigning from the position in September 1950 due to poor health.
He helped form the Middlesex Chamber of Commerce, and served as its president from 1925 to 1928.
He was a member of the Odd Fellows and the Grange, and served as a director of the Finger Lakes Association.
They had a son, Harold T.[17] Underwood died at home on December 8, 1950.