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Five Winter Trails Near Redmond

Winter is a great time to ride in Central Oregon!  Most lower-elevation trails are rideable year round, with sandy footing and impressive views of the snow-capped Cascades. Three of my favorite winter trails near Redmond are in the Cline Buttes Recreation Area, and two are in the Crooked River Grasslands northeast of Redmond.

Maston Area, Cline Buttes

Winter Trails Redmond, OR

With over 15 miles of easy, well-signed equestrian trails, Maston is a winter playground for Central Oregon riders.  Bikes have their own trails here, so while you may see cyclists go by on the bike trails, you won’t encounter them on the horse trails.  You can ride loops of varying lengths and enjoy sights including an old homestead, a historic canal, and two viewpoints overlooking the Deschutes River. 

Tumalo Canals Area, Cline Buttes

Winter Trails Redmond, OR

If you head east from the Tumalo Canals Trailhead, you’ll follow well-defined trails along a historic canal, over a low ridge, and on an old road with stunning views of the Three Sisters.  If you head west, you’ll encounter a network of dirt roads, canals, and user-created trails that offer many miles of unstructured riding.  

Fryrear and Dry Canyons, Cline Buttes

Winter Trails Redmond, OR

The non-motorized trails leading out of the Fryrear Trailhead will take you into Fryrear Canyon and Dry Canyon, which feature impressive outcroppings of tortured basalt.  (Note that Fryrear Canyon is closed from February 1 to August 31 to protect nesting raptors.  During the closure period, you can ride around the canyon, but not through it.  The trail closure is a serious business because the golden eagles nesting here will eat their young if you get too close to their nest.) In addition to the non-motorized trails, several OHV trails are nearby.  While OHVs are not allowed on non-motorized trails, equestrians are free to ride the OHV trails at their own risk.  

Warner Loop, Crooked River Grasslands

Winter Trails Redmond, OR

While the higher-elevation trails near Gray Butte are too muddy to ride in the winter without damaging them, the 12.5-mile Warner Loop Trail offers excellent winter footing.  This Crooked River Grasslands trail runs across sagebrush and bunchgrass flats, with nice views of Gray Butte, Pine Ridge, Haystack Butte, and Grizzly Mountain.  The hilly section on the west end of the trail provides views of Haystack Reservoir as well.  

Henderson Flat OHV Area, Crooked River Grasslands

Winter Trails Redmond, OR

The Henderson Flat OHV Area is a good place to ride in winter, because it’s closed to motorized use from December 1 to March 31.  The trails circle several buttes, run through the ravines that separate the buttes, and travel across the surrounding grasslands. 

So, don't stop riding just because the calendar says it's winter.  Just dress for the weather, and you can enjoy miles and miles of riding fun!

Learn More

Riding Central Oregon Horse Trails

You’ll find more information about these trails in Riding Central Oregon Horse Trails, by Kim McCarrel, available at

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