 In addition to his legal and business interests, Sherwood was active in the New York Militia as paymaster of Colonel Elisha Butler's regiment.Sherwood was elected as a Federalist to the Thirteenth Congress (March 4, 1813 to March 3, 1815).He was not a candidate for renomination to the Fourteenth Congress and resumed the practice of his profession in Delhi,

In 1830 Sherwood moved to New York City, where he continued to practice law until retiring in 1858.