Worland is named for Charlie "Dad" Worland, one of the first homesteaders in this part of the Bighorn Basin, and the manager of a stage station and saloon built along the old Bridger Trail in 1900. It wasn't wasn't much to look at - a cave dug into the riverbank, with log walls out front. His bar quickly acquired the title "The-Hole-In-The-Wall." A cigar box just behind the bar served as the local bank, and anyone needing money could borrow it and leave behind a I.O.U.

Originally located on the western side of the Bighorn River, Worland moved to the other side after the Chicago, Burlington, and Quincy Railroad announced plans to build along the east bank. The whole of Worland, 10 buildings, was slid across the river on the ice during the winter of 1905-06.