"Over the Oregon-Washington Highway from the Washington State Line, approximately four miles north of Milton-Freewater, southwesterly via Milton-Freewater and Adams to its junction with the Pendleton Highway, US30, at the east city limits of Pendleton; thence westerly over the Pendleton Highway (common with US30) to its junction with the Oregon-Washington Highway at S.E. 10th Street in Pendleton; thence southerly over the Oregon-Washington Highway to its junction with the Old Oregon Trail Highway, I-84, near Pendleton."
~ ODOT, Descriptions of US and Oregon Routes, March 2007
OR-11 was designated at the inception of the Oregon state route numbering system in 1932, but the OR-11 that exists today is a shadow of its former self. The OR-11 designated into the Oregon state route system spanned from the Washington border at Ferndale to the California border at New Pine Creek, traversing almost 400 miles of pristine Oregon terrain. It was routed along seven different state highways and passed through the towns of Pendleton, John Day, Burns, and Lakeview. However, OR-11's extremely lengthy designation would be short-lived thanks to US-395's extension south from Spokane, Washington all the way down to San Diego, California in 1935; as a result, OR-11 would become less than 10% its original length, a paltry 32 miles. With the exception of a 1.77 mile extension to I-80N (now I-84) in 1970, and a portion of old highway through Milton-Freewater that was bypassed to the east sometime after World War II, the route has pretty much stayed the same since 1935. Most of the original segments of OR-11 from Pendleton to New Pine Creek survive today as US-395, with a small section of the old OR-11 from Beech Creek to John Day permanently closed to auto traffic and converted to National Forest Trails. I will try and get information on that as soon as possible.
Unlike most other state highways, OR-11's mileposts run south-to-north, with its zero milepost at US-30 in Pendleton.
What was OR-11 in the 1940s or 1950s is shown in red. It ran from the junction of current OR-11 (S Main St. & SW 3rd Ave.) in Milton-Freewater (then just called Milton), wound its way through Freewater and then headed due north to end at State Line Rd. on the Oregon-Washington border; this highway used to connect to the Walla Walla Branch of Washington's PSH 3 and still connects to a road called the Old Milton Highway (not maintained by WSDOT). All of the 5.25 miles of highway used to be kept in the Oregon State Highway system as the Freewater Highway #339, but in January of 2003, maintenance of 1.82 miles of the highway was turned over to the city of Milton-Freewater. The next month, the entire former route was marked as OR-339, even though only 3.43 miles is still under state maintenance.