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Medford · United States

Cycling & running events in Medford, 2026

19events this year

19 races within 80 km of Medford

Road, trail, gravel, MTB — you name it, we've got it. Find something worth telling your friends about.

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A few races to know in Medford

We all need a goal — why not think big? Pick one and start training for it. Already happened this year? Find some practice races to build toward next year's edition.
Run·Road
Medford

Pioneer Road Run

The Pioneer Road Run takes place in November, starting at Phoenix High School in Phoenix, Oregon. It features a 9-mile race, a 5K, and a Pioneer Wheelchair 5K. The 9-mile race begins in the morning, with the 5K starting 30 minutes later. Both races must be completed by noon. The route follows public roads and trails that remain open to vehicle traffic. Participants should be mindful of cars on roads and paths. The event provides age-division ribbons, supports the Phoenix High School Cross Country team financially, and gives anniversary hats to the first 200 entrants. Commemorative pint jars are also available for purchase as an additional fundraiser.

Road
Bike·Track
Medford

Longest Day Mile

The Longest Day Mile is a one-mile track race held at Phoenix High School Track, run as four laps instead of a road loop. It is organized around evening heats sorted by expected pace, with separate groups for runners under 5:45, 5:46 to 7:00, 7:00 to 9:00, 9:00 to 11:00, and 11:00 minutes or slower. The setup accommodates different types of mile runners on the same night: fast runners aiming for a specific time, age-group competitors, and individuals preferring a more relaxed heat. Ribbons are awarded to the top three finishers in each age group, and a $100 prize is offered for any man finishing under 4:00 or any woman under 4:40. Entry is affordable, with online registration set at $13 and race-day entry at $15. The track is reserved strictly for registered runners: no headphones, dogs, baby joggers, bicycles, skateboards, or roller skaters are permitted.

Track
Bike·Gravel
Medford

Shasta Gravel Hugger

The Shasta Gravel Hugger is a March gravel bike race held in Montague, California, with Mt. Shasta visible from the routes. Participants can select the 100-mile Full Hug, the 100km Half Hug, or the 34-mile Handshake, accommodating century racers, shorter-distance riders, and younger participants. The course consists of approximately 50% gravel and 50% pavement, with road sections connecting ten distinct gravel sectors rather than a single continuous dirt path. The race evokes the character of a spring classic: pavement allows riders to spread out before the Northern California gravel sectors present a challenge. Jeep Road is noted as one of the more difficult sections, and the full course includes two significant climbs totaling about 4,700 feet of elevation gain. Weather conditions can be a factor; past events have featured snow, and one recent edition experienced a strong early headwind instead. The event is sanctioned by OBRA, has seen women start before the men, and past Full Hug winners include Rob Britton and Serena Bishop Gordon.

Gravel
About cycling & running in Medford

Medford Training Notes

Running: Locals run the Bear Creek Greenway when they want easy base miles, and the paved multi-use trail runs 20 miles between Ashland and Central Point through Talent, Phoenix, and Medford. Roxy Ann Park gives trail runners 15 miles of options, and Roxy Ann Peak stacks 800 feet of gain into the last half mile. The loop is 8 miles and hilly, running through oak groves and pine trees. Rogue Valley Runners has a Wednesday night group run from Hal’s shop. Southern Oregon Runners meets Tuesdays at 6 at Legends Cider in Talent. Tough as Nails, Rogue Run Marathon, Stagecoach Run, and Longest Day Mile anchor the calendar.

Cycling: Locals ride the Greenway for steady Z2, then point the bike toward Talent, Ashland, Jacksonville, and Gold Hill when they want longer road miles. Siskiyou Velo sets the club rhythm with more than 200 members and rides that vary by distance and speed. Team Cycle Sport, Ashland DEVO, and RVMBA keep the scene busy for road, youth mountain biking, and singletrack. Flywheel Honey Badger starts in Talent, and the hills west of town bring logging roads and a well-earned pint after. Greensprings Honey Badger starts about 30 miles east of Ashland. Takelma Gravel Grinder runs a 57-mile Bold route with 6,000 feet of gain.

Season: Medford trains well year-round, and September through May feels especially good for stacking base miles, trail days, and long rides. Summer brings Eastern Oregon-style heat, and the city averages 61 afternoons over 25°C and 11 afternoons over 30°C. Locals shift intervals early, keep Greenway spins honest, and save Prescott Park or Britt Woods for cooler windows. Winter stays milder than its latitude suggests because the Rogue Valley sits in a rain shadow between the Cascade Range and Siskiyou Mountains. Freezing temperatures happen on 64 mornings in an average year, so runners and riders still get out with layers from October 23 through April 23.

Upcoming

Coming soon in Medford

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
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What runners & riders are signing up for

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