Native of Cincinnati, Ohio. He later moved to West Virginia where he held the office of Circuit Court Judge in the town of Williamson.
Woolford moved to Ludlow in 1913. He served as mayor of Ludlow from 1922 to 1926 and was a vice president and director of the Ludlow Savings Bank. Woolford also served on the Ludlow School Board in the 1920s and was on the Board of Directors of the Northern Kentucky Semi-Pro Baseball League.
Woolford was married to Laura Buschmann, a native of Ludlow. He was the father of four children: Howard Woolford, Selma Woolford, Mrs. C.E. Hamersly, and Mrs. C.E. Adams. He died on August 7, 1931 at his residence (468 Elm Street). Burial was at Vine Hill Cemetery, Williamson, West Virginia.
Kentucky Post, November 11, 1921, p. 1,
January 13, 1925, August 8, 1931, p. 2; Kentucky Times-Star, March 17, 1928, p. 6.