From its beginnings, Wolsey stood at a crossroads in the heartland of South Dakota. In 1880, the Dakota Central Railway, a subsidiary of the Chicago & North Western, laid track along a wagon trail called the Black and Yellow Trail, now US Highway 14, named for its route from Chicago to the Black Hills and Yellowstone Country. In 1883, Magdalen Mosher platted Wolsey after acquiring the land from the railroad, and within two years the Chicago and Milwaukee Railroad, following what is now US Highway 281, laid track at the northwest edge of town at the Y junction. Richard Sears, later founder of the Sears and Roebuck Company, served there as a depot agent for the Chicago and North Western Railroad. In 1890, Wolsey contended to become the state capital, with railroad lands central to its campaign. The opening of the Kaneb Pipe Line terminal in 1964 made Wolsey a hub for gas-hauling companies, and the SD Wheat Growers grain terminal and Farmers Plant Food fertilizer storage facility along the BNSF Railroad have continued its role as a crossroads into the 21st century. Among people associated with Wolsey were Adolph Friese, who moved there in 1885, invented a machine to make cement blocks, erected the Friese Hardware Store, and with his wife helped start Wolsey Park; Richard Sejnoha, who opened his bakery and ice cream parlor in 1910 and patented the Universal Bread Sealer; Joseph Teply, who came in 1909 and managed the Hanskutt Lumber Company for 55 years; W.W. Howes, who began practicing law there in 1912, ran for governor of South Dakota in 1920, and later became First Assistant Postmaster General of the United States, with the Huron Airport named for him because of his efforts to secure commercial air service for South Dakota; Rev. F.W. Leyhe, who arrived in 1895 and served St. John’s Lutheran Church for almost 54 years, including 22 years of travel by horse and buggy to churches throughout the area; Richard Haeder Sr., who began farming near Wolsey in 1938, campaigned for grasshopper eradication and rural electrification, and became the Democratic nominee for governor of South Dakota in 1946; and Dr. M.E. Cogswell, who moved there in 1907, practiced medicine, and delivered more than 1500 babies over 53 years.