While Governor, Wolcott approved a bill authorizing the purchase by the Boston Elevated Railway the state-owned Tremont Street Subway tunnel, but required a public referendum on the proposed purchase. When it was brought to a vote, it was defeated by a 2-to-1 margin. When the Spanish–American War broke out in 1898, Wolcott immediately put the state on a war footing, securing legislative authorization for military expenditures in just 25 minutes. The state was one of the first to supply militia troops to the war effort.