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Theodore married, 2d, April 17, 1774, Pamela Dwight, daughter of Brigadier General Joseph Dwight of Great Barrington and his second wife, Abigail Williams (Sergeant) Dwight and granddaughter of Colonel Ephraim Williams, founder of Williams College, born June 26, 1753, died September 20, 1807 and the mother of his ten children. He married, 3d, November 7, 1808, Penelope Russell, daughter of Charles and Elizabeth (Vassall) Russell. She was born March 17, 1769, died May 18, 1827, at Boston and was buried in Mrs. Vassall's tomb under King's Chapel, Boston.
Theodore was but thirteen years old when his father died. Throught the assistance of his elder brother, John, he was enabled to attend Yale College for a time, although he did not graduate. After leaving college he took up the study of divinity but soon abandoned it for the law. He studied with Mark Hopkins of Great Barrington, Mass., the grandfather of Mark Hopkins, the distinguished later president of Williams College, leaving the home of his father at Cornwall, Conn., a distance of some twenty-five miles. He was admitted to the bar of Berkshire County, Mass., in April, 1776, and commenced practiced in Sheffield, Just across the border from Connecticut, and represented that town in the Massachusetts General Court or legislature. In 1776 he removed to Great Barrington and in 1785 to Stockbridge, Mass., where he made his home for the rest of his life. He built in 1785 at Stockbridge the Sedgwick House, which has remained in the family ever since, has recently been placed in the hands of trustees, two of whom are the great great grandsons of the Judge and a third who is the widow of another great great grandson. The purpose of this trust as stated in its preamble is "to maintain the House which for 160 years has sheltered descendants of its founder, Judge Theodore Sedgwick; to perpetuate a family tradition and to form a continuing bond between scattered members of the family."