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Early June in Oregon wastes no time getting busy. The first week of the month is packed with everything from low-key community 5Ks and themed fun runs to big mountain efforts, endurance challenges, and the early-season push into trail racing.
Portland and Eugene anchor the midweek slate with their continuing trail series, while Saturday brings the traditional “everything at once” Oregon race day—road races, trail ultras, triathlon festival racing, wine runs, and even a few novelty and charity events all stacking up across the state.
It’s one of those weekends where you could stay in one region and race, or hop between very different experiences entirely.
| Race Name | Date | Location | Distances | Registration Links |
|---|---|---|---|---|
| Portland Trail Series – Spring | June 3, 2026 | Portland, OR | 6M, 4M | More Information |
| Emerald City Trail Series | June 4, 2026 | Eugene, OR | 8M | More Information |
| Best in the West Triathlon Festival | June 6–7, 2026 | Sweet Home, OR | Triathlon, Duathlon, Relay, 13.1M, 10K, 5K | More Information |
| Butte Challenge | June 6, 2026 | Hermiston, OR | 10K, 5K | More Information |
| Run for Life | June 6, 2026 | Vancouver, WA | 10K, 5K | More Information |
| Conquer the Canyon | June 6, 2026 | Redmond, OR | 13.1M, 10K, 5K | More Information |
| Dirty Half Marathon | June 6, 2026 | Bend, OR | 13.1M | More Information |
| Doggie Dash | June 6, 2026 | Salem, OR | 5K | More Information |
| Elijah Bristow 24/12 Run | June 6, 2026 | Dexter, OR | 24H, 12H | More Information |
| Lebanon Strawberry Run/Walk | June 6, 2026 | Lebanon, OR | 5K, 1M | More Information |
| Oregon Brewery Running Series – Ruse | June 6, 2026 | Portland, OR | 5K | More Information |
| Santiam Hospital Fun Run | June 6, 2026 | Stayton, OR | 10K, 5K, 3K | More Information |
| Starlight Run | June 6, 2026 | Portland, OR | 5K | More Information |
| Timberline Marathon and Half Marathon | June 6–7, 2026 | Mount Hood, OR | 26.2M, 13.1M, 14.4M | More Information |
| Turtle Trot | June 6, 2026 | Ashland, OR | 10K, 5K, 1M | More Information |
| Wicked Wine Run – Left Coast | June 6, 2026 | Rickreall, OR | 5K | More Information |
| Feed Newberg 5K | June 7, 2026 | Newberg, OR | 5K | More Information |
| Mt. Ashland Hill Climb Run | June 7, 2026 | Ashland, OR | 13.3M | More Information |
| My Breast Friends 5K | June 7, 2026 | Eugene, OR | 5K | More Information |
| Pink Duck 5K | June 7, 2026 | Bend, OR | 5K | More Information |
| R2L Bridge Run | June 7, 2026 | Rainier, OR → Longview, WA | 10K | More Information |
| Run for the Hills | June 7, 2026 | Corvallis, OR | 30K, 8K, 2M | More Information |