Oregon

Click on a pin to see the route name and a short description of the route. An alphabetical listing of all routes with detailed information is just below the map.

Central Oregon
(within a 2-hour drive of Bend)

Big Summit Prairie Loop
Short
A mix of scenic mountain prairie and  Ponderosa forest. A classic spring ride.
Loop: 48 miles /  3800 feet
Style: Mixed (1 gravel sector, 21 miles)
Where: About 24 miles east of Prineville, OR
Long
The short version + more gravel + more distance + more elevation!
Loop: 69 miles / 4900 feet
Style: Mixed (1 gravel sector, 41 miles)
Where: About 30 minutes east of Prineville, OR

Billy’s Playground
Roubaix option
A classic century ride with quiet roads and a bit of gravel thrown in!
Loop: 97 miles / 5300 feet
Style: Roubaix (??)
Where: Sisters, OR
Gravel option
Mountains, Lakes, rivers and creeks and pure fun!
Loop: 67 miles / 3800 feet
Style: Mixed (3 gravel sectors, 31.5 miles total)
Where: Sisters, OR

Catch & Release!
Circumnavigate the Freemont Canyon with a classic wilderness crossing of Wyches creek.
Loop: 37 miles / 1700 feet
Style: Mixed (2 gravel sectors, 15 miles total)
Where: Sisters, OR

Donnybrook
Explore one of the most remote parts of Oregon. Expansive. Big. Scenic. Demanding.
Loop: 54 miles / 4400 feet
Style: Mixed (1 gravel sector, 19 miles total)
Where: ~ 15 minutes northeast of Madras, OR

Eastside Training ride
A great spring / fall training. The beginning and ending terrain dictates a slower pace, but the middle section of the ride can be as fast and hard as your desire.  
Loop: 43 miles / 1500 feet
Style: Mixed (5 gravel sectors, 13 miles total)
Where: Bend, OR

Ghost of Ashwood
Ride through some of the most scenic ranching country in all of Oregon!!
Loop: 44 miles / 4300 feet
Style: Mixed (1 gravel sector, 25 miles)
Where: ~ Madras, OR

GravelCracker
* 60
Explore one of the most diverse and scenic areas to ride in Central Oregon. Nothing too extreme. This ride is a true favorite!
Loop: 58 miles / 2900 feet
Style: Mixed (4 gravel sectors, 27.4 miles total / 3 single-track sectors, 13 miles total)
Where: Sisters, OR
* 85
The ‘big brother” to the 60. This includes a traverse along the southeast shoulder of Mt. Jefferson through the 2003 B&B Complex burn area.
Loop: 85 miles / 5200 feet
Style: Mixed (5 gravel sectors, 45.2 miles / 2 single-track sectors, 9 miles total)
Where: Sisters, OR

In Plain View
* Short (working  –> pics)
Big mountain views, all gravel.  A classic winter ride.
Loop: 25 miles / 925 feet
Style: Gravel
Where: Bend, OR
Long
Big mountain views, with a little more mileage and some pavement.  A classic winter ride.
Loop: 33 miles / 1200 feet
Style: Mixed (3 gravel / double-track sectors, 26 miles total)
Where: Bend, OR

Jailbreak
Roll up and over the Baldwin hills, through some of Oregon’s wild country and past several remote and scenic farms. Then a long descent back, with outstanding views of the Cascade mountains.
Loop: 33 miles / 2400 feet
Style: Gravel (mostly)
Where: Madras, OR

McKay Creek Lollipop
A classic (4.5+ star) spring time ride! Wildflowers, flowing streams, green grasses and just pure fun.
Lollipop: 38 miles / 3700 feet
Style: Mixed (2 gravel sectors,  20.5 miles total)
Where: Prineville, OR

Mitch & Walt
A big ride, with big returns!  Great views, lightly traveled roads, and a mid-ride stop in Mitchell, OR.
Loop: 64 miles / 5600 feet
Style: Mixed (2 gravel sectors,  36 miles total)
Where: About 20 minutes east of Prineville, OR

Oktoberfest
One of our favorite fall rides in the Bend area. Colors! Good gravel roads!
Loop: 36 miles / 2200 feet
Style: Gravel
Where: Bend, OR

O’Leary Landslide Loop
A big climb! Beautiful views! And one of the best gravel descents in the region!
Loop: 56 miles / 5500 feet
Style: Mixed (1 roubaix sector, 14 miles / 1 gravel sector, 24 miles)
Where: McKenzie Bridge, OR

Path of Totality
Gorgeous lakes, two buttes, an old railroad grade and a super cool descent!
Lollipop: 41 miles / 3000 feet
Style: Mixed (2 gravel sectors, 4 miles total / 1 double track –> single track sector, 6 miles total)
Where: ~ 15 min from Madras, OR

Priest Hole
Painted Hills + the John Day River = Kick Butt gorgeous
Loop: 37 miles / 3200 feet
Style: Mixed (2 gravel sectors, 14 miles total)
Where: Mitchell, OR

Post35 / Post46
Some of the best gravel in Central Oregon.  Attack the 9-mile climb that gives back huge sweeping views of the Crooked River plains.
Loop: 35 miles / 2900 feet … or 46 miles / 3000 feet
Style: Gravel (mostly)
Where: Post, OR

Quick & Dirty
A great after work training ride!
Loop: 20 miles / 1300 feet
Style: Gravel
Where: Bend, OR

Sherman’s March
The Camp Sherman area is one of the most diverse and scenic areas to ride in Central Oregon. Pure heaven!
Loop: 52 miles / 4000 feet (Several shorter options are detailed in the route description.)
Style: Mixed (5 gravel sectors, 31.4 miles total / 2 single-track sectors, 4.7 miles total)
Where: Camp Sherman, OR

Two Bulls, One Indian
The real deal.  Demanding, steep, and off the beaten track.  So good.
Loop: 58 miles / 3800 feet
Style: Mixed (2 gravel sectors, 28 miles total)
Where: Bend, OR

Twin Bridges – Roubaix option
The classic Twin Bridges route with a little gravel thrown in!
Loop: 36 miles / 2500 feet
Style: Roubaix (3 gravel sectors, 6.5 miles total)
Where: Bend, OR

Water & Lava
The best entry-level gravel / adventure ride in the area. Absolutely beautiful.
Loop:30 miles / 1400 feet
Style: Mixed (3 gravel sectors, 17.5 miles)
Where: Bend, OR

Westside Tour
Another great entry-level ride that wanders past / through: First Street rapids, the North River trail, Shevlin Park, Phil’s Trailhead, Good Dog Park, River Bend Park, Miller Park, and Drake Park.
Loop: 25 miles / 1300 feet
Style: Mixed (5 gravel sectors, 9.4 miles total / 8 bike path sectors, 7.9 miles total)
Where: Bend, OR

4 Boys!
A highly variable (and fun!!) route with over 20 different sectors ranging from paved road, to gravel road, to doubletrack, to singletrack, to paved bike path. 
Loop: 46 miles / 2500 feet
Style: Mixed (8 gravel sectors, 14.3 miles total / 7 single track sectors, 12.5 miles total / 3 paved trail sectors, 14.3 miles total)
Where: Bend, OR