A highly entertaining ride, this loop never ventures more than about an hour from Bend, but showcases some of the best the high desert has to offer. Highlights include the Crooked River and O’Neil highways.
Go east on Alfalfa Market Road to Southeast Reservoir Road until you get to OR 27. Go north (left) on OR 27 down into the Crooked River Gorge and on into Prineville. From Prineville, take the O’Neil highway to NE 33rd Street, then go north on 33rd to NE Smith Rock Way. Follow this road west to Terrebonne. At Terrebonne, go North on 97 about a mile to Lower Bridge Road on the left. Head west on Lower Bridge Road to Holmes Road and then take Holmes road to 126. At 126, go west into Sisters. From Sisters, take US 20 back to Bend.
Alfalfa Market Road
The 15 miles between Bend and the small farming community of Alfalfa include a long section of high-speed sweeping curves that, while being great fun on a motorcycle, have proven treacherous for automobiles as you’ll see by the crosses dotting the roadside.
Crooked River Highway (OR 27)
Like all good motorcycle roads, the Crooked River Highway strikes the perfect balance of incredible scenery and long stretches of twisty pavement. The river below is a favorite for fishermen and campers, so watch for wayward pedestrians and their pets. The first 15 miles is bordered by the river and rock walls. Rocks and gravel frequently find their way onto the best sections of pavement, so use caution as your throttle hand gets twitchy. A two-mile section marked 20 MPH a few miles from the dam is highly technical and should be ridden with care.
O’Neil Highway (OR 370)
The O’Neil Highway winds along between the bordering rim rock and the City of Prineville Railway—a 19-mile stretch of track built and paid for by the citizens of Prineville around 1918. Watch for views of Smith Rock—a favorite Central Oregon climbing destination—to the north as you ride through the farmland along NE Smith Rock Way.
Lower Bridge Road to OR 126 and Sisters
Lower Bridge Road has several moderately technical sections, but this older roadway suffers from frost heave and much of it has been patched with tar which doesn’t offer much traction in warm weather. Holmes Road is in somewhat better condition, but offers a different danger in the form of open range—which means that around that perfect bend in the road ahead you could find a herd of cattle. ‘Nuff said.
Sisters is a western-themed tourist town. The many festivals and events during the summer make the going slow as the streets crowd with people and people-watchers. Mid-June is rodeo time and it’s best to avoid the area during rodeo weekend.
US 20 from Sisters to Bend
US 20 is a fairly straight stretch of road with moderate traffic. Traffic tends to move a bit faster, but this last leg of the trip is the most scenic, making it a good road to kick back and cruise. A viewpoint about midway between Sisters and Bend offers unparalleled views of the South, Middle, and North Sisters mountains and is well worth a stop.
View Bend, Oregon – Prineville – Sisters Loop in a larger map