When you cycle out of the narrow Rogue Valley, you’ve got nowhere to go but up. The Siskiyou and Cascade mountain ranges separate this deep thumbprint of timberland from the rest of the state; the long rides are as spectacular as they are punishing. Make your home base the upscale town of Ashland, on the southern end.
GREAT RIDE: Butte Falls/Prospect loop, a favorite of the local Siskiyou Velo cycling club, climbs about 1,600 feet in elevation into the Cascades, snaking along the Rogue River on the way back.
BIKE SHOP: Siskiyou Cyclery.