Distance: 37.1 miles
Just 30 minutes from Bend, Oregon, Sisters is a quaint Western town where the social calendar revolves around the annual rodeo and the country's largest quilting show. Settle into the haute-rustic FivePine Lodge, then get ready for big views. "Leaving the mountainous country around Sisters and riding into the high desert of central Oregon along the Deschutes River, it's just beautiful," says ultra-endurance cyclist Gregg Geser, a local who does laps on this rural run to train. Smooth pavement, minimal traffic, and a steady loss in elevation (300 feet) can have you blazing along at 25 mph. On the day Geser let me tag along, a 45-mph tailwind let us easily hit 35 without pedaling for miles at a time. The ride turns perpendicular to the wind here and there – we had our bikes leaning 45 degrees at one point to fight it. But the only real obstacle lies in the distraction of river pools begging for hand-tied flies and wildlife preserves full of beaver, otter, and eagles. Don't forget to pack your rock-climbing shoes: The ride ends among the sport-climbing crags of Smith Rock State Park.
More information: To start from the airport, have guide Whit Bazemore of Ride Cycling Tours pick you up, drive you 25 miles to Smith Rock, and shuttle your luggage while you rip it east to west. You'll look nonstop at the Three Sisters, a trio of 10,000-foot, snow-capped volcanoes, and finish in downtown Sisters, where you can hit the Open Door wine bar for dinner.