Skull Hollow

5 Star Route / Published April 2020

What we like about this ride …. it typifies Central Oregon! The route includes peekaboo views of Smith rock, incredible views of the Cascades range, and a chance to ride over the historic Crooked River (High) bridge and look down into the impressive gorge.

Adventure / Gravel Route

– Loop: 28 miles / 1900 ft gain
– Surface: ~ 30% gravel, 70% paved
– Technical Difficulty: Moderate-
– Tire Size (recommended minimum): 40 mm
– eBike Friendly: Yes
– Location: ~ 30 minutes north of Bend, OR

RideWithGPS | Strava | GPX File | Cue Sheet

When we like to ride this …

Spring when the Cascade mountains are snow capped. Fall when the colors are changing. The route is rideable almost anytime of the year, but the area can be very busy in the summer. Avoid when wet.

Food & Water


The Start

Across the street (north) from the Terrebonne Depot restaurant, on the dirt road. This is 16th street and public; it is a short section of dirt road gets no traffic. Do not use the Terrebonne Depot restaurant parking lot, but do get a burger and beer there after the ride!
Lat / Long: 44.352490, -121.172475


Research, writing, and media by LindaE and KevinE, co-founders of Dirty Freehub.

Terrain & Riding: What to expect …

A mix of terrain, from ranch and farmlands to punchy hills overlaid with grasses and scattered Junipers on the north shoulder of Gray Butte. But this route is also chock full of history and big views; the Central Oregon Cascade Mountains to the west and buttes to the north and east including Haystack butte, Grizzly Butte, and Gray Butte.

The route is more pavement than gravel, but don’t be fooled into complacency. The gravel roads are of the primitive forest service type with a bit of gnar and the Grey Butte climb and descent are steep, which will push the limits of some (Can you say “hike-a-bike”?).

Highlights and Navigation

~ mile 5.5 / Tricky Navigation

The biggest navigation challenge of the day is making your way across the Crooked River Gorge and Highway 97. At the dead end circle, pass between a set of rocks marking the road boundary, go straight for 25 yards on a dirt path to the knee high rock wall marking the cliff to the Crooked River Gorge. Take the paved path to the right to the High bridge. Cross it and then continue to follow the paved path to Highway 97. Cross the highway, and then proceed north along the highway for 20 to 40 yards. To your right you will see the old highway, or as it is called today the Culver highway. This is the road you want. Look for the concrete barriers and barb wire fence. Just to the right of the barriers is an opening in the fence that you want to take.

~ mile 5.5 / Crooked River Gorge

The Crooked River Gorge is a 500-foot-deep gorge through which the Crooked River flows., The cliffs are made of columnar basalt eroded by the Crooked River since the Newberry volcanic eruption 1.2 million years ago.[Wikipedia]

~ mile 5.5 / Crooked River High Bridge

The Crooked River (High) bridge is 464 feet long, and at 295 feet above the river it was the nations single highest arch span when constructed. Oregon’s famous bridge engineer, Conde B. MCCullough, designed the bridge to blend gracefully with the regions rugged landscape — harmonizing with the Oregon Trunk Line Railway bridge of 1910, just downstream. [from on-site kiosks]

~ mile 5.5 / Crooked River Railroad Bridge

This bridge was designed by the famous bridge architect, Ralph Modjeski, who also designed the San Francisco–Oakland Bay Bridge. The bridge was a critical juncture in the Oregon Railway wars which had two competing rail lines building track from the Columbia River to Bend, Oregon.[Wikipedia]

~ mile 8 / McPheeters Turf Farm

An ongoing working sod farm and nursery that is an exemplar of family farming in Central Oregon. In Central Oregon, there are approximately 2500 farms on 1.7 million acres of land producing an agricultural market value of $141 million dollars each year.[, Oregon State University]

~ mile 11 / Big Views of the Cascade Mountains

Here you will get some of the best views of the Cascade Mountains in all of Central Oregon including the Three Sisters and Mt Jefferson.

~ mile 12.7 / McCoin Orchard

In 1886, Julius and Sarah McCoin homesteaded this area with a 160-acre tract with a well-functioning spring. Early settlers depended on fruit orchards, which provided a long harvest season, to feed their families.

People who settled in the area surrounding Gray Butte built homes, planted crops, set up businesses, and built an elementary school that was about 9 miles from here. But the homesteading boom came to an abrupt end in the 1930s when a 10-year drought made it all but impossible for people to sustain themselves on their land.

Because the homesteaders, many of whom were also struggling from the effects of the Great Depression, couldn’t support themselves, they stopped paying their taxes and in some cases simply walked away from their land. It was at this point that the federal government stepped in and repurchased the land, first for cattle grazing, and later establishing the Crooked River National Grasslands.[Bend Bulletin: August 7, 2012]

~ mile 15 / Skull Hollow

In 1864 American soldiers came across 40 burned out wagons, china, and the bones of 200 human remains in the area. It is believed that this was from a battle between settlers of the Meeks Wagon Train and Native American Indians. Thus, the name Skull Hollow.[]

~ mile 25 / Smith Rock

At ~ mile 24, we strongly recommend you make the right to Smith Rock state park. It is only a mile out of the way and the views are amazing and its fun to diverge a bit and watch the climbers moving over the vertical walls of stone like little ants.

This landscape of rock spires, cliffs, and canyonlands lies along the northern edge of the Crooked River caldera, a 26-mile long, 17-mile wide volcanic depression formed through a series of super-volcanic eruptions between 29.7 and 27.5 million years ago. Eruptions from the Crooked River caldera deposited massive volumes (>140 cubic miles) of tuff and rhyolitic lavas, dikes, and domes. All of these volcanic features are now well exposed in the rock walls of Smith Rock State Park.[Terrebonne Depot for a good post-ride meal and drinks.

Route Notes

1) Do not ride when wet. It looks like this could be the real sticky kind of mud, of the ‘hike a bike” variety.
2) We recommend the use of a red blinky light with rear looking radar detector, like a Garmin Varia. Several roads have light to moderate traffic.

Route Options

If you are looking for a longer ride that is really, really good we recommend Haystacks & Skulls.


Love Where You Ride!

The northern tier of this ride is through the Crooked River National Grasslands. Between 1880 and 1930 much of this land was tilled up for farming after it was mistakenly reported that the land was suitable for dryland farming. By 1930, after a 10 year drought, nearly 700 homesteaders had moved out. The grasslands were returned to government ownership through the purchase of non-performing homestead lands in 1960s.

Today, the grasslands provides habitat for 375 species of wildlife including deer, elk, antelope, mountain lion, songbirds, waterfowl, and raptors including the threatened Northern Bald Eagle and the endangered Peregrine Falcon. 

One of the lead organizations working to protect these lands and others like it is Discovery Your Forests. Check them out!

The Ride

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