What’s not to love about a high-desert town with about 300 days a year of sunshine and trails that start conveniently in the
center? Rent a mountain bike from Sunnyside Sports (sunnysidesports.com) and head to Phil’s Trail, on the west edge of town, where the network of paths runs the gamut of difficulty and passes through ponderosa pine forests.
Or hike or run through downtown and Drake Park on the Deschutes River Trail. Smith Rock State Park, north of town, has sheer basalt walls and welded tuff cliffs that make it a magnet for rock climbers.
Where the athletes eat: Get your morning brew at Backporch Coffee Roasters (541/617-3984). Jackson’s Corner ($; 541/647-2198) has wood-fired pizzas, sandwiches, and, on Thursday nights, killer burgers with seasonal ingredients like local morel mushrooms.