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Wife Mercy Freeman's death preceded his. She died September 28, 1711, and was buried beside him in Cove Burying Ground. Mercy Freeman (nee Prence) was the granddaughter of Elder William Brewster. Thus the Freeman family became a bloodline Mayflower family.

During his adult lifetime, some specific titles and activities he was involved in include: Elected a freeman of the Colony in 1651. Lieutenant, Captain, and Major. Active part in the Indian Wars. Ensign, Waltham, MA, 1654.

Major in the expedition against the Indians at Saconet, 1677.

Member of the Council of War, 1667-76.

Captain in the fight against the Indians in Taunton, 1675 Major of the Barnstable group, 1685. Deputy for Eastham, eight years. Selectman, 1663-73.

Assistant Governor, Plymouth Colony 1666, for several years

Appointed to the bench of Common Pleas, 7 December 1692. Deacon of the Eastham Church for many years. His family intermarried into families well known subsequently in genealogy: Merrick, Sparrow, Payne, Mayo, Knowles. This is detailed in his will and inventory which follows.