CheddarHead
5 Star Route
Tillamook, Oregon
Tillamook. Synonymous with dairy. This ride explores what makes Tillamook what it is. Mountains, valleys, rivers, bays, and farms, oh my! But be warned, this is one of the most difficult and demanding rides that we have ever posted! Read this guide in detail.
Route: Loop | 90 mi
Gain: 10,900 ft
Surface: 60% gravel / 20% single-track / 20% paved
Technical Difficulty: Very Demanding
Navigation: Attention Required
Locale: Extremely Remote
Tire Suggestion: 50 mm+
eBike Friendly: No
GravelCracker (The Overlander)
5 Star Route
Sisters, Oregon
The ‘big brother” to the GravelCracker. Includes a traverse along the southeast shoulder of Mt. Jefferson through the 2003 B&B Complex burn area and a trip up to Round Lake (super scenic, but rough!).
Route: Loop | 77 mi
Gain: 4,800 ft
Surface: 50% gravel/dirt rd, 20% single-track, 30% paved
Technical Difficulty: Demanding
Navigation: Attention Required
Locale: Remote
Tire Suggestion: 45 mm+
eBike Friendly: No
Kloochman
5 Star Route
Prineville, Oregon
A mixed gravel century (almost a century) that includes the Crooked River Canyon scenic bikeway, the Maury Mountains, and the Post / Paulina road. This ride links two of the best paved roads in Central Oregon with a gravel segment through ranching and farming country and some national forest.
Route: Loop | 92 mi
Gain: 4,400 ft
Surface: 40% gravel road, 60% tarmac
Technical Difficulty: Very Demanding
Navigation: Attention Required
Locale: Remote
Tire Suggestion: 40 mm
eBike Friendly: Yes
Steens Mountain Loop Road
5 Star Route
~ Burns, Oregon
The Steens Mountain Loop Road departs the tiny, historic town of Frenchglen and climbs up Oregon’s eighth-tallest mountain on a tour of massive gorges, vast panoramas and one of the most spectacular lakes in the Pacific Northwest.
Route: Loop | 72 mi
Gain: 7,300 ft
Surface: 85% gravel, 15% paved
Technical Difficulty: Moderate
Navigation: Straightforward
Locale: Remote
Tire Suggestion: 45 mm+
eBike Friendly: Yes
The Bishop
5 Star Route
~ Bend, Oregon
Get ready for a big ride with a bit of everything: gravel roads, forest service dirt roads, dropbar single-track, and some pavement.
Route: Loop | 100 mi
Gain: 7,000 ft
Surface: ~ 65% gravel , 20% single-track, 15% paved
Technical Difficulty: Very Demanding
Navigation: Attention Required
Locale: Remote
Tire Suggestion: 40 mm
eBike Friendly: No
