Skull Hollow

5 Star Route / Ridden and Reviewed by Gravel Girl & Captain ‘O

Chief Paulina was a ruthless warrior and the strategist behind a bloody outcome in 1864 that left over 200 dead in the area. Besides visiting this famous battleground, the route also 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.

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”?).

Saving the best for last, you end at a local brew pub! The Terrebonne Depot. **Click to Read More

Adventure / Gravel Route

Loop with dogleg: 28 miles / 1900 ft gain
– Surface: ~ 30% gravel, 70% paved
eBike Friendly: Yes
– Location: ~ 30 minutes north of Bend, OR
– Date Posted: April 2020 (Updated March 2021)


Moderate. Due to the primitive Forest Service roads with steep grades of up to 15%.

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.

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

Food / Water



Wahoo / Garmin Direct Download
Cue Sheet / GPX FileTCX File


Red = paved road
Brown = gravel / dirt road
Purple = paved bike path / roubaix

For help with GPS files, the RideWithGPs mapping app and to learn how to download our routes for free, see the “Using Our Rides” page.

  • Ricardo Villalobos says:

    The only tricky part was finding the entrance to SW Culver Hwy after crossing 97 (look to the right of the gate). Definitely a tough climb, particularly with temperatures close to 100 degrees. The descent requires some expertise, since there are many rocky segments hard to navigate. I used 40-inch tires, but could’ve benefited from 44s… although there’s plenty of road, so maybe a good compromise. Also, the trail is super isolated, with nobody else within sight for many miles… not the best idea to do this alone.

  • Matt Rhoades says:

    FYI Oliver Lemons has ZERO bike racks, however I concur the staff was welcoming to me and allowed me to bring my bike into the store.

    • KevinE says:

      Any chance you could drop a quick email to them asking for bike racks and explain why? That would help out the DF Team. Thanks!

  • Just passing this on as FYI
    on route support. No affiliation.

    Cyclist who stay as guests with us at Spoke’n Hostel in Mitchell, tell us (rave actually) that the folks at Oliver Lemons Market,
    love cyclist! Great place to check out for water bottle refills, delicious deli and shopping, a place you can bring your bike into or lock it up as I understand.
    Sit down or take out options.
    phone: 541.382.3940

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