Distance: 174.5 miles
Difficulty: Challenging

Pioneer homesteads, winding rivers, tiny Western towns under red-rock buttes in the high desert – few American landscapes evoke the 19th-century frontier more than remote, central Oregon. The classic Prairie Hotel in the tiny village of Prairie City, Oregon, marks the beginning of this two- to three-day counterclockwise loop through the entire Old West Scenic Bikeway. From there, inn-to-inn cycling takes you through rural ranchland so remote and lacking in amenities that prudence calls for booking a food-stocked cabin in advance at the Boulder Creek Ranch in Bates. Roll in late on that first night, cook dinner with the provisions that are already waiting for you, and then wake early to enjoy fresh eggs from the coop. Cruise all morning along the quiet curves of the John Day River, where chinook salmon spawn after swimming 480 miles upstream from the Pacific. A stunning, 9-mile descent – ideally, free of the meandering wild turkeys I encountered – sweeps you into Monument, an isolated town situated beneath stately mountains, where the Monument Motel & RV Park offers mid-ride lodging. Then it's a big, 61-mile day past the John Day Fossil Beds (Day was a fur trapper who joined the Lewis and Clark expedition from St. Louis to Oregon in 1810, then stuck around) to Mount Vernon, where you can rest your head at the Bike Inn. An easy, 21-mile spin the next day gets you back to Prairie City in time for steaks at the Oxbow Restaurant & Saloon.

More information: Call Mike Cosgrove, the local proponent of this route (he put up all of its "Scenic Bikeway" signs) for goings-on in the area on the days you'll be there: 541-620-2250.