Looking for the best cycling in Oregon? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Oregon. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Cycling Spots in and near Oregon

  • Corvallis, Oregon

    Mary's Peak

    52 mi / 4020 ft gain
    This ride takes you from the banks of the Willamette River at the Corvallis waterfront to the top of Mary's Peak, 26 miles and 4,000 vertical feet away. While it starts out with a warm-up through the flats of the Willamette Valley, it quickly starts climbing up around the west side of Mary's Pea...
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  • Portland, Oregon

    Run Springwater Corridor Trail

    7 mi / 50 ft gain
    Springwater Corridor is a 40-mile paved trail that stretches from downtown Portland all the way to Boring. This trail is wide, virtually flat, and yes, paved - but there is a clear manmade path on the dirt shoulders that's friendlier to knees. Any given day, you'll see dozens of cyclists and pede...
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  • CRATER LAKE, Oregon

    Bike around Crater Lake

    I forgot how large Crater Lake was. Wikipedia said it was only 6 miles in diameter, multiply X 3.14 or C = πd and boom its only 18.84 miles around, that's cake, or pie. Imaging a NASCAR track with a pond in the middle.WRONG, hindsight being 20/20, dramatic landscape rarely equates to flat, cycle ...
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  • Sisters, Oregon

    The Sisters to Smith Rock Ride

    36.6 mi / 597 ft gain
    Starting in the "Old West" town of Sisters, Oregon and ending at Smith Rock State Park outside the small town of Terrebonne, this route takes riders past a variety of historical sites, shows the gentle curves of the Deschutes River and frames spectacular views of the Cascade Mountains, and ends w...
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  • Bend, Oregon

    Ride the Twin Bridges Loop

    Starting and ending at Drake Park in the heart of downtown Bend, the Twin Bridges Loop is one of the most popular and scenic road cycling routes in Central Oregon.The Twin Bridges Loop covers 36 miles of rolling terrain and offers breathtaking views of the snow-capped Cascade mountains, rolling f...
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  • Hood River, Oregon

    Bike from Hood River to The Dalles

    40 mi / 2800 ft gain
    The ride from Hood River to The Dalles is one of the best 20 mile stretches of road biking in Oregon, and arguably the best. The ride starts out in the wonderful town of Hood River - a tourist and adventure destination in its own right - and follows the historic Columbia River Gorge highway (US-3...
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  • West Linn, Oregon

    Run Old River Road to George Rogers Park

    4.8 mi / 100 ft gain
    Portland and its surrounding suburbs are filled with trails and hidden treasures, including this stretch along the Willamette River. This road is a super popular pedestrian path and can be accessed from West Linn, the Mary's Woods and Marylhurst Development, or from Lake Oswego off of Highway 43....
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  • 11020 Southwest Denney Road, Oregon

    Run the Fanno Creek trail

    4 mi
    The parking lot marked is at the North end of the Fanno Creek trail, you can get on the paved path here and put on just about as many miles as you want! With the help of google maps on your phone you can follow trail hop all the way down to Tualatin! But if you're looking for a shorter workout yo...
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  • 7444-7498 Southwest 160th Avenue, Oregon

    Bike the Westside Regional Trail

    8 mi
    Technically this trail stretches from the Tualatin Hills Nature Park, down through the west Beaverton/ Sexton Mountain area and can comfortably get you to Barrow’s park near Big Al’s. The trail from end to end comes in at just over 8 miles, so a down and back by bike can make for a good workout a...
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  • Port Orford, Oregon

    Bike the Wild Rivers Scenic Bikeway

    60 mi / 3000 ft gain
    The Wild Rivers Scenic Bikeway starts and ends in Port Orford, and includes stops at Port Orford Heads, the Wild and Scenic Elk River, and Cape Blanco. It's a perfect ride for anyone looking to see the highlights of the section of coast around Port Orford without spending the whole day in the car...
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