Cheboygan marks the entrance to nearly forty miles of an inland waterway of rivers and lakes ending about eight miles from Lake Michigan at Crooked Lake. Native Americans first used this path to avoid the rough waters of Lake Michigan, and later European settlers used it for industry and recreation. Steamers such as the Flora traveled the Great Lakes from 1875 to 1912, commonly making round-trip journeys from Cheboygan to surrounding islands and St. Ignace while lumber mills on the river shared the waterway with commercial cruises. The mills processed white pine harvested from the region's vast forests, and in 1847 Jacob Sammons and Peter McKinley built Cheboygan's first steam mill. The last log drive on the Cheboygan River was captured by a local photographer in 1910. The 1877 iron swing bridge at State Street in Cheboygan, later replaced in 1940 by a double-leaf bascule bridge on US-23, is now listed in the National Register of Historic Places. The North Central State Trail mile markers follow the Michigan Central Railroad's numbering system, which began in Bay City at mile 0 and ended in Mackinaw City at mile 182, placing Cheboygan at mile 156.