The only question is which riders have it better here, the roadies or the mountain bikers?
Why I Chose It: Ashland is celebrated for its annual Shakespeare Festival, but this southern Oregon town deserves to be just as famous for its biking. The only question is which riders have it better here, the roadies or the mountain bikers? Road cyclists have the 55-mile Cascade Siskiyou Scenic Bikeway, which begins and ends downtown and climbs 5,000 feet out of Bear Valley, with views of iconic landmarks like the volcanic Pilot Rock and the 9,000-foot tall Mount McLoughlin.