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Five Winter Trails Near Redmond

If you live in Central Oregon near Redmond, you have access to several fun winter trails that are rideable year round.  Three of my favorite winter trails near Redmond are in the Cline Buttes Recreation Area.  Two others are in the Crooked River Grasslands northeast of Redmond.

Five Winter Trails Near Redmond
Henderson Flat OHV Area

The Cline Buttes Recreation Area is 50 square miles of BLM land situated between Bend, Redmond, and Sisters.  The terrain has little elevation change, and the footing is sandy – perfect for winter riding.  You can access the non-motorized trails from several trailheads, as described below.

Five Winter Trails Near Redmond
Dry Canyon

Maston Area, Cline Buttes

With over 15 miles of easy, well-signed equestrian trails, Maston is a winter playground for Central Oregon riders.  Bikes have their own trails in this area, 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 canyon.  You can reach the Maston Trailhead on Newcomb Road, east of Cline Falls Highway.

Five Winter Trails Near Redmond
Settlement Trail, Maston Area

Tumalo Canals Area, Cline Buttes

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.  You can reach the Tumalo Canals Trailhead on Barr Road, west of Cline Falls Highway.

Five Winter Trails Near Redmond
Tumalo Canals Area

Fryrear and Dry Canyons, Cline Buttes

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.  The Fryrear Trailhead is on Fryrear Road, between Hwy. 20 and Hwy. 126.

Five Winter Trails Near Redmond
Dry Canyon

Warner Loop, Crooked River Grasslands

While many of the 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.  You can access the Warner Loop Trail from either Cyrus Horse Camp or the Scales Corral Trailhead, off Laurel Lane north of Redmond.

Five Winter Trails Near Redmond
Warner Loop

Henderson Flat OHV Area, Crooked River Grasslands

The Henderson Flat OHV Area is a good place to ride in winter, because it’s closed to all 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.  You can access the trails from the Trail Crossing Corral Trailhead at the end of Park Lane, off Hwy. 97 north of Redmond.

Five Winter Trails Near Redmond
Henderson Flat OHV Area

Learn More

You’ll find more information about these trails in Riding Central Oregon Horse Trails, by Kim McCarrel, (Ponderosa Press, 2012), available at

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