Woolf was elected to the Legislative Assembly of the Northwest Territories in the 1902 election, defeating Heber Simeon Allen in the district of Cardston. He served in this capacity until 1905, when the new province of Alberta was created out of part of the Northwest Territories. Though in keeping with territorial custom Woolf had served as an independent in the territorial legislature, federally he was a Liberal, and in the debate over whether Alberta's politics should be conducted on an independent basis or along party lines, he was a strong advocate of the latter option.