With some of the most scenic training routes you’ll ever encounter and a lively foodie (and microbrew!) culture, Oregon’s high desert is a huge draw.
In summer or fall—the city sits at more than 3,600 feet, so it has a high-desert environment with about 300 days of sunshine every year.
You can get to Bend’s Redmond Municipal Airport via one of four airlines (American, Alaska, Delta, United) with a direct flight from Denver, Los Angeles, Portland, San Francisco, Salt Lake City or Seattle.
The cozy rustic-meets-simple luxury Hilton Garden Inn is conveniently located in the Old Mill District, steps away from more than 30 stores and plenty of restaurants. (Rooms start around $180/night.) Hiltongardeninn.com