Self-educated eldest son of a farmer and religious seeker, Winchester began preaching to the New Lights of the Congregationalist Church in his native Massachusetts as a youth. He soon joined the Baptists, where he married the first of what would become his five successive wives. At a revival meeting in 1771, he was ordained a Baptist minister in Rehoboth, Massachusetts. In 1774, Winchester traveled to Welsh Neck, South Carolina to accept a position, which he left upon the death of his first wife. He married again in Boston, but that wife too died, as did his third wife in 1779. Seven of his eight children also predeceased him. As an itinerant preacher, Winchester grew increasingly troubled about slavery. In a 1779 revival meeting, he preached to fifty whites and about a hundred blacks, one of the first to share the gospel openly with slaves. He discovered solace in the Everlasting Gospel of Paul Siegvolck and Universal Restitution of George Stonehouse, Oxford Holy Club alumni like John Wesley, and came to believe inuniversal salvation. Winchester decided to stay in Philadelphia after stopping there on the way back from a Massachusetts vacation, and receiving invitations to preach from a white church and a black church. He also eventually married for the fifth time. After the Baptist Church excommunicated his 100-member congregation in 1781, Winchester founded the Society of Universal Baptists and preached at the University of Pennsylvania for four years before a meeting-house could be built on Lombard Street. Winchester also became acquainted with Unitarians, including the physician George de Benneville, who had fled France and Germany to a safe haven near Ephrata, Pennsylvania. The two traveled on missionary tours through Pennsylvania, New Jersey and Virginia. During what became a six-year trip to England, Winchester preached at least twice daily and worked with William Vidler to transform the General Baptist Assembly. In the end the Assembly excommunicated Vidler for universalist tendencies in 1793. Winchester also met Joseph Priestley, Thomas Belsham and Richard Price, and published The Universal Restoration: Exhibited in Four Dialogues in 1788. During his absence, American Universalists including his friend Benjamin Rush had held a Convention in 1790 and established their own church. Winchester returned to New England in 1794 for a preaching tour and became moderator of the Massachusetts Universalist Convention. He then returned to Philadelphia in 1796, where he drew Priestley to American shores and shared his pulpit, but fell ill with tuberculosis. He gave a major sermon to the Convention in Hartford, Connecticut, and several lesser sermons, before his death on April 18, 1797 aged 45.