A.J. Warrin Road was established in 1879 as an alternate route from the Santiam Wagon Road (Willamette Valley and Cascade Mountain Military Road). Early pioneers had to go from Sisters Country to Prineville to buy supplies they couldn’t grow, hunt or gather, make, or make a trade for. Road building was a business, tolls were charged and the builder hoped to get something back on his investment. A.J. Warrin figured out a more direct route than the Santiam route from Cache Creek through Camp Polk and Lower Bridge. His road went southwest of Black Butte, across Wychus Creek (Squaw creek) near what is now Sisters and due east to Cloverdale. It went along the north side of Fryrear Butte and into the uplands between Deep Canyon and the Deschutes River where it crossed at Tetherow Crossing (also established in 1879). It met Crooked River at Carmicle where it rejoined the Willamette Valley and Cascade Mountain Military Road following the river to Prineville. White and yellow paint on rocks, trees, and posts marked each mile along the route. Parts of it had been known as Tetherow Bridge Road, Redmond Sisters Road, South Redmond Sisters Road, and Jordan Road.

The original documentation from the Crook County road records reads:

“Now, on this day was submitted to the Court a Petition of A.J. Warrin et al. praying for the location of a County road commencing at a point on the road leading from Prineville to Summer Lake three fourths of a mile west of main Street in said town thence down and on the South & West side of Crooked river to Mr. Carmicle house thence as herein prayed for to intersect the Willamette Valley and Cascade Mountain road at a point between Black Butte and Dry Creek…”

Once a well traveled route, it provided an alternative route between the Black Butte area and Prineville than the Santiam Wagon Road, which went through Camp Polk. From Sisters the A.J. Warrin Road went to Cloverdale, which became an important stop on the long route to Prineville. Oscar Maxwell filed on the land in Cloverdale where A.J. Warrin Road linked with the Camp Polk route. He established a stopping place for travelers and their stock and a store for locals. His store and other services, including a smithy, became vital to the emerging community. Later the Cyrus family bought out Maxwell and ran the rest-stop until gradually, with changes in transportation and growth of nearby Bend and Redmond, the route came into disuse.

Hatton, R.R.
1996 Oregon’s Sisters Country: A Portrait of Its Lands, Waters, and People. Maverick Publications: Bend, OR
Deschutes Country Roads, Legacy Roads Information.