Bend:   Bend is the place to ski! Amazing hill climbing up 9th street to Awbrey Butte, although the descent will put hair on your chest and take skin off everything else. Skyliners road, out and back, is an excellent upgrade on the way out, and pleasant, even exciting downhill on the way back. If you go to the end of the road it’s about 16 miles. Or, you can ski up to Mt. Bachelor. It’s best to do early in the morning as the road gets way hot later (at least in the summer). The total distance is 22 miles, but there are lots of places that make for great natural stopping points. You do need a shuttle, unless you want to ski down which means real screamers.  -Stuart Craig

Near Bend: This one is my go-to and absolutely fantastic: Sunriver Lava Butte Trail  -Mike Karlovich

Corvallis Oregon: Corvallis has stellar roller skiing. Oak Creek Drive is several miles round trip. Nice pavement. Wide shoulder. The bike path to Philomath is perhaps 15 miles round trip. Lots of good, paved farm roads.  -Rob Root

Jackson County: Bear Creek Greenway is an 18-mile paved trail runs from Ashland through Talent, Phoenix, and Medford to Central Point. -Michael Dawkins

Redmond: Dry Canyon Trail -Mike Karlovich