Skull Hollow

5 Star Route

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.

Scroll to Top