Oregon Bicycle Ride Calendar

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Updating to 2023

Click the month for bike ride dates, locations, mileages, and sponsorships …


New Year’s Day Ride, Breakfast on the Bridge


Worst Day of the Year Ride


Wet ‘n’ Windy


A Cherry of a Ride, Pedals and Pears, Filmed by Bike, Monster Cookie Metric Century …


Pedal for People, Ride of Silence, Reach the Beach, Columbia Gorge Explorer, Century Ride of the Centuries, Umpqua Ultimate Bike Ride  …


Pioneer Century (formerly Spring Century), Three Rivers, Tour de Hood, Pedalpalooza, Strawberry Century Tour, No Frills Century, Tour de Fronds, Gorge Ride, Ashland Weekend, Petal Pedal, Mountain Lake Challenge, Northwest Tandem Rally, Prairie City Invitational…


Cycle Oregon Weekend, Oregon Ride to Defeat ALS, Tour des Chutes, Ride Through Paradise, Oregon Bicycle Ride, Jackson’s Ride the Gorge …


Bike Oregon Wine Country, Tour des Trees, Bike MS Oregon – Willamette Valley, Blackberry bRamble Century, Alpine Century Covered Bridge Bicycle Tour, Recumbent Retreat, Cascade Gran Fondo, Crater Lake Century, Portland Century, Bike to Beer Fest, Lancette Memorial Ride, Yaquina Lighthouse Century


Cycle Umpqua Vineyard Tour, Cycle Oregon, People’s Coast Classic, Tour de Lab, Ride the Rogue, Farm to Farm Century, Hood River Fall Century, Harvest Century


Handmade Bike and Beer Festival… 

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  1. Hello,

    How would I go about adding our events to your on-line calendar? Thank you for your time.


  2. Hi!
    I would like to announce the first annual “Pedals ‘n Pears” cycling event coming to Medford on April 9th. How do I add it to your calendar?
    For anyone interested: here’s the site: http://www.pedalsnpears.com

    hope to see you out there!


  3. Looking forward to spreading the word so that cyclists can squeeze one more Metric Century before the end of the summer… The Oregon City Metric Century — Ride It or Recycle It!

    If you’d like to check us out, find our website at http://www.ocmakeitorbreakit.com.

    How do I spread the word through http://www.bikingbis.com?

    Thank you.


  4. Get in one more metric century ride before Fall! Tour de Outback Aug 13th Lakeview OR ! Check it out at lakecountychamber.org and come see a part of Oregon you probably have never seen…” More critters than cars!”

  5. Hello from the McCloud Chamber of Commerce,

    Please include the following information in your race calendar for 2017:

    9/23/17 McCloud Bike-toberfest: McCloud, CA. A variety of mountain bike and road bike rides, plus the ever-popular cyclo-cross races. Rides take place on both public and rural roadways, including the Great Shasta Rail Trail. Rides finish in downtown McCloud at the Bike-toberfest Festival. Riders and attendees will enjoy live music, brats, and beer while strolling through a variety of craft booths. Fore more information and to learn how to register, please visit http://www.mccloudchamber.com/mccloud-events//bike-toberfest or call (530)964-3113.


    • Sandi Brown on January 21, 2017 at 12:54 pm
    • Reply

    Please consider Ride the Heart of the Valley in Corvallis on April 29, 2017. It’s run by veterinary students, a great route, uncrowded, and for a super cause (funds for veterinary care for pets whose owners can’t afford it).

    See: http://ridetheheart.weebly.com/

  6. Hi!

    I’m back again to announce the 2nd “Pedals ‘n Pears” cycling event coming to Medford on Saturday, April 8th. Last year we had over 300 riders and it was a great success.

    For anyone interested: here’s the site: http://www.pedalsnpears.org

    hope to see you out there!


    • Tami Hart on March 1, 2017 at 8:52 am
    • Reply

    Explore a different part of Oregon by heading over to Eastern Oregon for the “Great Owyhee Ride Against Hunger” which benefits the Oregon Food Bank – Southeast Oregon Services. See some of the beautiful sights Eastern Oregon has to offer on June 10, 2017. Last year, we had more than 250 riders and are expecting more this year.

    Here’s the registration site link:


    Happy cycling!

      • Philbo on January 31, 2020 at 10:20 am
      • Reply

      I am hearing that this ride is once again happening in 2020. Is this correct?

        • Rusty on March 7, 2021 at 7:03 am
        • Reply

        no go, cancelled like so many others.



    Join us this September for the Umpqua Vineyard Tour offering 5 cycling routes to appeal to riders of all ages and abilities. Routes range from 15, 30, 50 half century, 75, to 100 mile century. Meet other people like yourself on lightly traveled rural roads that follow the beautiful, scenic Umpqua River. Cyclists will view dozens of vineyards, forests, fields, mountains and orchards along the way, with opportunities to visit local wineries and tasting rooms. Friendly rest stops at scenic locations with nourishing food and snacks. Fun for the entire family!


    A team consists of 3 or more riders. It can be your friends, family, employees or co-workers or a combination. Have your employer sponsor your team.

    • Ron Hilbert on March 12, 2018 at 4:11 pm
    • Reply

    The Vineyard Tour in Roseburg has joined “Great Umpqua Outdoor Days” and moved our date to Sunday September 2nd Labor Day Weekend for 2018.
    All rides start 7 – 9 AM at Discovery Garden next to River Forks Park.
    The Vineyard Tour Road Bike Ride is a cycling event held each September sponsored by Umpqua Velo Cycling Club and offers 5 cycling routes to appeal to riders of all ages and abilities.


    Many Roads. One Purpose.

    The Tour de Cure is an event where no matter what road you take, you will be joining thousands of people from around the country who have the same passion as you to fight diabetes and its burdens.

    All riders, runners and walkers will be treated to lunch and a fantastic celebration party for all to enjoy.

    The Tour de Cure is bigger and better than ever with options for everyone.

    Here’s where to register and learn more:


    Hope to see you there!

    • Pat Kaczmarek on February 13, 2019 at 3:43 pm
    • Reply

    Cascading Rivers Rides for 2019 – Please add to your events calendar!

    Faraday Moonlight Ride – Saturday, August 17, starts at 10:00 PM, $10
    12 mile fun ride along the Clackamas River and several lakes on a road closed to traffic. The ride is fully supported with prizes, free group picture and after ride party in a brew pub or lounge.

    Three Cascading Rivers Rides on the Last Weekend in September
    Killer Fang Ride Starts at 8:00 AM on September 28th, $95.
    A 2 day 144 mile (72 each day) ride to Detroit OR and back with an overnight in a campground or a stay at cyclists expense in a lodge or motel. Ride is along the Cascading Rivers Scenic Bikeway.

    Raging Rapids Ride Starts at 10:00 AM Sunday, September 29th, $45.
    Your choice of 35 or 52 mile routes along the wild and scenic Clackamas River’s whitewater rapids.

    Register online at: https://www.bikereg.com/cascading-rivers-rides
    Event Phone: (503) 630-3401

  9. Oregon Bicycle Ride Calendar—-> Please add this event to your website calendars

    Bikes N Brews
    Website: https://www.downtownmedford.org/bnb-routes
    Saturday, October 15th, 2022
    Registration @Coldwell Banker Pro West Real Estate
    Location: Parking Lot
    Address: 300 E Main St
    Hours: 7:00am
    First ride: 7:30 am

    Rides start on East 8th St. at South Riverside connecting to the Bear Creek Greenway in Hawthorne Park.

    Five Routes. All Distances start and end in the Downtown Medford as part of The Heart of the Rogue Festival.

    Contact Information

    Richard “Barney” Bauernfeind

    Start Location
    Coldwell Banker Pro West Real Estate, 300 E Main St, 97501, Medford, Oregon, United States

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