Haystacks & Skulls

5 Star Route

This is a 5 Star Route, meaning that it is a highly curated, premier riding route.

This ride is the blend of two 5 Star routes: Haystack and Skull Hollow. Of the 3 routes (Haystack, Skull Hollow, and Haystacks & Skulls) this is Captain O’s favorite! Big views, fast riding pavement with little traffic, and some challenging gravel climbs.

For a complete take on the ride, please review the Haystack and Skull Hollow route descriptions along with the the ride details below.

Adventure / Gravel Route

Loop with dogleg: 35 miles / 2300 ft gain
– Surface: ~ 35% gravel, 65% paved
eBike Friendly: Yes
– Location: ~ 30 minutes north of Bend, OR
– Date Posted: April 2020 (Revision History: last updated March 2021)

Terrain & Technical Difficulty[what this means]

Moderate. 35% Primitive BLM dirt road. 55% Flat and fast pavement.

The primitive BLM roads have uphill grades of 15%, slightly less on the downhill side. The area is at the urban / rural interface of Central Oregon.

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: 44.351354, -121.173055

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.


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

Ride Details

Start in Terrebonne and follow the Skull Hollow route to mile 7.4, the right turn to McPheeters Turf farm. Instead, continue straight along the Culver highway tracking the Haystack route. Ride the dirt road segment through the Crooked River National Grassland, past Haystack reservoir, and then back on gravel and south towards Grey Butte. Begin climbing. Part way up the climb, just after the incredible views of the Cascade mountains, make a 90 degree left. You are now back onto the Skull Hollow route. Follow this to the summit, descend Skull Hollow, and then roll back on pavement towards Smith Rock and the start / finish.

Food / Water


Ride Notes

40 mm tires are more than sufficient for this ride.

Do not ride when wet. It looks like this could be the real sticky kind of mud, of the ‘hike a bike” variety.

We recommend the use of a red blinky light. Several roads have light to moderate traffic.

Ride Options

There are two shorter options to consider: Haystack and Skull Hollow. Haystack is the technically easier ride.

Ridden and Reviewed by …

Gravel Girl / Team Dirty Freehub

She loves a good day of gravel, like most people like a good book. She’s always amused by the outdoors and the wild adventures. Gravel Girl is a Co-Founder of Dirty Freehub.

Captain O / Team Dirty Freehub

He should have “Never Stop Exploring” tattooed on his chest! He loves adventures on bikes and is a Co-Founder of Dirty Freehub.

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