"Over the Crooked River Highway from its junction with the Ochoco Highway, US26, in Prineville, southerly via the Crooked River and Bear Creek Canyons to its junction with the Central Oregon Highway, US20, approximately seven miles west of Brothers."
~ ODOT, Descriptions of US and Oregon Routes, March 2007
OR-27 was created at the beginning of the Oregon state route system in 1932. Its original routing began on Warm Springs Highway #360 at the small central Oregon town of Metolius at the junction of old US-97 (then a portion of The Dalles-California Highway #4, now OR-361, Culver Highway #361) and continued across many county roads (roughly along US-26's current path) through Prineville south along the Prineville-Bear Creek Highway #14 (roughly along OR-27's current path) south to US-20 near Brothers. On July 19, 1940, the northern portion of OR-27 is reclassified as a primary state highway, decommissioning the Warm Springs Highway #360 moniker in favor of the Warm Springs Highway #53 (confused yet?). I don't know when the Madras-Prineville Highway #360 was created, as well as when the current alignment was built; I'm guessing sometime around the time US-26 was designated in Oregon.
Speaking of which, the Metolius-Prineville section of OR-27 was deleted when US-26 was extended into Oregon in 1952. Additionally, in 1961, the Prineville Reservoir and Bowman Dam were built, requiring an entirely new highway to be built around the reservoir. Once completed, the highway was redesignated as the Crooked River Highway #14, the name it has today. Since then, it's pretty much remained the same old mostly-unpaved road for the past 40+ years. Personally, I think it's a useless designation south of the reservoir, but if you want to take the road less traveled, OR-27 is the way to go.
In 1941, OR-27 ran from US-97 in Metolius to US-20 near Brothers. Note that none of the routing is paved.
OR-27 is moved onto a new section of highway coinciding with the opening of a new alignment of US-97 in 1948, with a new northern terminus south of Madras. The entire routing between Madras and Prineville is now paved.
OR-27's routing is shortened to its current termini in 1952 with the extension of US-26 into Oregon, as evidenced in this 1958 map. Note the pre-resevoir routing.
A portion of OR-27 was put underwater in 1961, requiring a new routing near Taylor Butte as shown in this 1965 map. The majority of the highway is still not paved.
This is the routing of OR-27 as of 1977. It looks as if the Prineville Resevoir receeded a little bit, enough to create a state park along its old alignment. It also could be because maps still were not computerized at the time.
This is the current routing of OR-27 as of 2005. The route is now paved all the way to the crossing of Bear Creek, but still leaves 18½ miles unpaved on its southern end. I hope it never gets paved.
It is important to note that all map segments are copyrighted by their respective owners, and that these map segments are used for educational and historical purposes only. Hosted by ImageShack.
A portion of old OR-17 exists between Metolius and Lamonta, which disappeared in the 1950's. Through route reconstruction, I believe the highway, shown in red, left Metolius eastbound along 6th St., then turned south along SW Columbia Dr., then turned into SW Eureka Ln., then followed SW Bear Ln. crossing the current right-of-way for US-97 (a small section is missing where they had to make the road intersect US-97 at proper angles). After that, the road's actual route gets a little hazy; a new map will be put up with my new route reconstruction.