Undated photo of the Steinman overcrossing, south of Ashland, Jackson County, Oregon. Built in 1914, it's the earliest known bridge constructed along the route of the then-proposed Pacific Highway in Oregon. It is also the only known switchback on the Oregon highway system -- that is, the only instance where the highway crosses over itself. I've included a couple of excerpts from a 1941 and a 1971 straightline chart showing how the OSHD/ODOT decided to represent the loop.
...this segment became US-99 in 1926 and remained so until 1938, when it was bypassed to the west. It was kept in the state highway system (as Siskiyou Highway #273) on February 18th of that year by the Oregon State Highway Commission. It did not carry a route designation until December 11, 2002, when the OSHC's successor, the Oregon Transportation Commission, numbered it OR-273.
The railroad it crosses belonged to the Oregon & California Railroad at the time, controlled by Southern Pacific since the Siskiyou Summit line was constructed in 1887. Southern Pacific wouldn't own the railroad outright until January 3, 1927. Southern Pacific sold the line to the Central Oregon & Pacific Railroad on December 31, 1994. They continue to operate the line to this day.
Posted by Jonathan Ledbetter to the Historic US Highway 99 Facebook group, March 4, 2020
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