Fry served in several units during the duration of the Revolutionary War, participating in 10 major battles including the Second Battle of Trenton, the Battle of Princeton, and the Battle of Red Bank in 1777.
In 1778, He joined many other men of color who formed the 1st Rhode Island Regiment in what became known as the 2nd Rhode Island Regiment. They returned to Rhode Island and bravely participated in the Battle of Rhode Island. After fighting at the Battle of Yorktown in 1781, Fry continued to serve until the conclusion of the war in 1783.
Fry married an American Indian woman, Lucy Davis, and spent the remainder of his life in Rhode Island. The two had at least five children. Fry applied for a pension in 1818, and although he was promised a land grand of 100 acres, he never received it. Fry passed away in 1823 and was laid to rest in East Greenwich. The Rhode Island State Society Daughters of the American Revolution honor Winsor Fry and all of our patriots of color, whose dedication to the cause played a pivotal role in the American Revolution.