The Best Cycling in Bend

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

Top cycling spots in and near Bend

  • Bend, Oregon

    Ride the Twin Bridges Loop

    4.5
    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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  • Sisters, Oregon

    McKenzie River Pass Full Day Ride

    38 mi / 2191 ft gain
    The 38 mile McKenzie Pass ride is without a doubt the most spectacular bike ride in the entire state of Oregon. The ride begins at the Village Green Park in Sisters, Oregon, along Oregon Route 242, which is a stretch of roadway included on the U.S. Register of Historic Places. The route heads wes...
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  • Sisters, Oregon

    The Sisters to Smith Rock Ride

    5.0
    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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