In the age of the auto trail , the roads that later formed US 2 through the UP were given a few different highway names . When the original roadways between Ironwood and Iron River were completed in late 1915 , the Upper Peninsula Development Bureau ( UPDB ) named the area Cloverland and the highway the Cloverland Trail . Later the name was extended over the highway to Escanaba , and to all highways in the area in the early 1920s ; the name was phased out by the UPDB completely in 1927 . The roadways were also used for the Theodore Roosevelt International Highway , named for former US president Theodore Roosevelt after his death in 1919 . Overall , this highway ran from Portland , Oregon , to Portland , Maine , by way of Michigan and the Canadian province of Ontario . Through the UP , the southern branch followed the immediate predecessors to US 2 , including the section through Florence County , Wisconsin .