Jackson was born in Brighton, Massachusetts, to Samuel and Mary Wright (Field) Jackson. He was educated at the public schools of Brighton and the Massachusetts Institute of Technology, where he took the full course with the Class of 1868 but left without degree on May 4, 1868, when he received employment on the staff of the City Engineer of Boston. His first work was on the construction of the Chestnut Hill Reservoir of the Boston Water-Works. In 1870 he became Engineer for the Town of Brighton, and also engaged in private practice until Brighton was annexed to Boston in 1873, when he again entered the office of the Boston City Engineer. During the next three years he was engaged on various works, including surveys for the introduction of water into Brighton and West Roxbury. From 1876-1885 he was Assistant Engineer on the Boston Main Drainage Works, an important and difficult engineering undertaking.
