Kilpatrick was born in White Plains, Georgia. He had an orthodox upbringing and was educated at Mercer University and Johns Hopkins University where he later became a mathematics teacher at High School and at Mercer University. He first met John Dewey in 1898 and again met him in 1907. Kilpatrick decided to make philosophy of education his specialty and occupied all courses by Dewey. From this developed a cooperation, which persisted up to Dewey's death in 1952. Both men's ideas directly impacted the 1932 founding of Bennington College in Vermont: they were both on the original College Board of Trustees, with Kilpatrick soon becoming President of the Board, and two of the original 12 houses on campus are named after them.