Century Rides in Oregon
The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Oregon.
Cycling in Oregon: Terrain & Route Overview
Oregon is widely celebrated as one of the most progressive and scenic cycling states in the world, featuring the nation's only official State Scenic Bikeway program. Century riders here can pedal beside dramatic Pacific sea stacks on the Oregon Coast Highway, climb volcanic passes around Mount Hood and the Three Sisters in the Cascade Mountains, or tour rolling vineyards in the fertile Willamette Valley. In Central and Eastern Oregon, sunny high-desert routes wind past dramatic basalt canyons in Smith Rock and along the John Day River. The summer and early autumn seasons offer dry, mild weather with long daylight hours. Exceptional cycling infrastructure, thriving craft breweries at every finish line, and unmatched environmental beauty make Oregon a world-class century cycling destination.
Terrain Characteristics: Pacific Coast cliffs, Cascade volcanic passes, Willamette Valley wine country, and high-desert canyons.
Riding Season & Weather: May through October (Year-round coastal routes).
📍 Oregon Century Rides Map
22 Plotted EventsBike MS Oregon (Ride the Valley)
SeptemberScenic charity century winding past lush vineyards, rolling hazelnut groves, and historic wine country.
Blackberry Bramble Century
AugustScenic tour winding along the scenic North and South Umpqua rivers, timberlands, and rolling vineyard country.
Cascade Gravel
MayThe Cascade Gravel is one of the most scenic and diverse gravel events in the country, providing an amazing ride through the Central Oregon high desert and Cascade Mountain Range.
Columbia Century Challenge
JuneEmbark on a fully supported cycling adventure through the breathtaking back roads of picturesque Columbia County in NW Oregon.
Crater Lake Century
AugustA challenging century ride with breathtaking views of the surrounding Cascade mountains and Crater Lake, benefiting local charities.
Gorge Gravel
AprilGorge Gravel is a 100-mile gravel ride that takes place in the foothills of the Cascade Range and through the Mount Hood National Forest, featuring silky smooth gravel, constantly changing scenery, and routes naturally sheltered from the Gorge's notorious spring winds.
High Cascades 100
July100 Miles with an old friend or new one in Bend, Oregon
Joyride
JuneA women-centric weekend of bikes, natural splendor and belonging. Every Body. Every Bike. Every Joyride.
Monster Cookie Metric Century
AprilEarly-season classic touring through scenic farmland, hazelnut orchards, and river crossings of the Willamette Valley.
Oregon Coast Gravel Epic
AprilThe Oregon Coast Gravel Epic is a challenging gravel ride along the Oregon Coast. The ride features a 100-mile route and is open to riders of all skill levels.
Oregon Gran Fondo
MayOne big day in Cottage Grove will bring together cyclists of all skill levels and backgrounds to celebrate the biking community. On the third Saturday of May, cyclists will bike distances of 100 miles in the Gran Fondo, or 70 miles in the Medio Fondo.
Peach of a Century
SeptemberLate-summer harvest century traversing rolling country roads, hop fields, and fruit orchards around the Mid-Willamette Valley.
Pioneer Century
JuneThe Pioneer Century has a 50-year heritage with the Portland Bicycling Club (formerly Portland Wheelmen Touring Club). The Pioneer is named to reflect the history of the Champoeg, Canby, and Molalla areas. Rich farmland and timber brought the pioneers to this area, and this same beauty draws cyclists today.
Real West Gravel
MarchKick off your season in Pendelton, Oregon for the long route at Real West Gravel. The long route is 67.7 miles.
Ride the Rim
SeptemberRide, run or walk on vehicle-free days at Crater Lake National Park, with a safe space to enjoy the park on two wheels, one wheel, or by your own feet.
Ride the Rogue
SeptemberA celebration of cycling with a party, supporting the Rogue River Greenway Trail. Options for all levels of riders, with excellent support and refreshments.
Sasquatch Duro Gravel
AprilAmazing loop close to PDX & Carlton, Oregon, is a wonderful community.
Skull 120/60/30 Gravel Grind
JuneThis is a not-for-profit event supporting the Public Lands of Harney County. The Skull 120/60/30 Gravel Grind route highlights the county's rugged character which sets rural #EasternOregon apart from the rest of the nation.
The Art of Survival Century
MayA supported mixed surface ride through quiet rural roads, exploring Southern Oregon’s Klamath Basin and Northern California’s Tulelake Basin and Butte Valley region, with informational rest stops highlighting local geology, cultural history, geography, and environmental issues.
The Vineyard Tour
OctoberRide through diverse scenery including multiple vineyards and bodies of water. Experience the Umpqua Valley's beauty and charm.
Tour de Fronds
JuneThe Tour de Fronds is one of the most beautiful cycling events in Oregon. The Tour is your choice of scenic rides on low-traffic roads in Southern Oregon’s beautiful Coast Range, with views of old-growth forests, wildflowers, waterfalls, rivers, streams, and mountain vistas.
Tour de Pear
AprilPedal for a Cause at the Tour de Pear Bike Event