[1] Jackson moved to Barre City, Vermont, where he supported himself by giving piano, organ, and music composition lessons while studying law.[4][5][6][7][8] In 1901 he was elected Barre's Grand Juror (municipal court prosecutor) and he served as Washington County State's Attorney from 1904 to 1906, succeeding John H.[16][17] The 1905 citizenship court case against S. Hollister Jackson arose as an attempt to disqualify him from serving as State's Attorney for Washington County, Vermont.The Vermont Supreme Court heard the case in early 1906, with both sides presenting extensive arguments on naturalization laws and citizenship by descent."[22] His tenure was marked by efforts to strengthen Vermont’s future through a policy initiative called "The Citizens and Leaders of Tomorrow"[23] which aimed to retain the state’s youth and curb outward migration.[28] During the Great Vermont Flood on November 2, 1927, Jackson's car stalled after he hit a deep hole while attempting to drive through the rising Potash Brook near his home at Nelson and Tremont Streets in Barre.
Lt. Gov. S. Hollister Jackson died in the 1927 flood of Vermont after getting out of his car.