He was made a Freeman in Milford, Conn. on 11-May 1671. He probably remained there until after the death of Mary, when he returned to Farmington. Here he held a number of local offices. He was chosen “hayward” in 1682 (in charge of fences around public pastures) and later. In 1683 he had a brand issued to him “for neat, sheep, & swein....a swallow Cropp in ye near ear & hors a halfpenny in ye under sied of ye near ear”.
At a court of Election held in Hartford 13-May-1686...”John Rue having appealed from the judgment of the Court of Assistants, wherein they freed Mathew Woodrofe from being the reputed father of the child that Hannahm the now wife of sayd Rue, the Court having heard what hath been presented to them, see no reason to alter or vary from what the Court hat done”.

The estate of Mathew Woodruff in vol. 1 of “earrly Conn. Probate Records, Hartford District” was inventoried 18-May-1691 by John Orton and John Lee and amounted to 334-08-02. The children were listed thus: “Mathew Woodruff about 23 years old, John about 19 years old, Samuell 14 years next April, Nathaniell about 5 years, Jospeh about 2 1/2 years, Mary neere 21 years old, in firm in her legs, Sary about l17 years, Hannah about 10 years old, Elizabeth about 12 years.”