Late May keeps the variety coming, mixing weekday trail series races with unique challenges like stair climbs and scenic destination half marathons in Eastern Oregon. From ridgeline trails in Eugene to small-town road races and mountain-backed courses, this stretch offers a little bit of everything as the season rolls toward summer.
| Race Name | Date | Location | Distances | Registration Links |
|---|---|---|---|---|
| Anchor Run 5K | May 2, 2026 | Warren, OR | 5K | More Information |
| Walk/Run for the Animals | May 2, 2026 | Vancouver, WA | 5k | More Information |
| Bend Beer Chase | May 2, 2026 | Bend, OR | 55M Relay | More Information |
| Firelane Trail Trial | May 2, 2026 | Portland, OR | 4.5M | More Information |
| Hearts With a Mission Superhero Run | May 2, 2026 | Valley of the Rogue State Park, OR | 10K, 5K, 1M | More Information |
| Lake Oswego Lake Run | May 2, 2026 | Lake Oswego, OR | 10K, 5K | More Information |
| Lost Creek Trail Run | May 2, 2026 | Trail, OR | 50K, 30K, 5K, 30K Relay | More Information |
| Loyalty Day Run | May 2, 2026 | Newport, OR | 1M | More Information |
| McDonald Forest 50K Trail Run | May 2, 2026 | Corvallis, OR | 50K | More Information |
| Oregon Brewery Running Series – Xicha | May 2, 2026 | Eugene, OR | 5K | More Information |
| ORRC Hagg Lake Run | May 2, 2026 | Gaston, OR | 10.5M, 10K | More Information |
| OSU CVM Pet Day 5K Fun Run/Walk | May 2, 2026 | Corvallis, OR | 5K | More Information |
| Tree Planting 5K and Fun Run | May 2, 2026 | Oakridge, OR | 5K, 3K | More Information |
| Cinco de Mayo Half Marathon | May 3, 2026 | Portland, OR | Half Marathon, 10K, 5K | More Information |
| Halfway Half Marathon & 10K | May 3, 2026 | Halfway, OR | Half Marathon, 10K | More Information |
| Sisters Country | May 3, 2026 | Sisters, OR | 50K, Half Marathon | More Information |
| Portland Trail Series – Spring | May 6, 2026 | Portland, OR | 6M, 4M | More Information |
| Bend Trail Series | May 7, 2026 | Bend, OR | 4M | More Information |
| COCC Jungle Run | May 7, 2026 | Bend, OR | 4M, 2M | More Information |
| CARDV 5K Fun Run/Walk | May 9, 2026 | Corvallis, OR | 5K | More Information |
| Dam Good Run | May 9, 2026 | McNary, OR | 10K, 5K | More Information |
| Doggie Dash | May 9, 2026 | Portland, OR | 2.5M | More Information |
| Halsey Library Book-It! 5K | May 9, 2026 | Halsey, OR | 5K | More Information |
| Happy Girls Half Marathon | May 9, 2026 | Bend, OR | Half Marathon, 10K, 5K | More Information |
| Hippie Chick | May 9, 2026 | Champoeg State Park, OR | Half Marathon, 6.6M, 5K | More Information |
| Mud Factor – Medford | May 9, 2026 | Medford, OR | 5K | More Information |
| Race to Space | May 9, 2026 | McMinnville, OR | 12H, 8H, 6H, 3H, 1H, 6M Relay | More Information |
| Silverton Fun Run | May 9, 2026 | Silverton, OR | 5K, 1M | More Information |
| STRIDE 5K | May 9, 2026 | Salem, OR | 5K | More Information |
| Oregon Track Club Running Series #3 | May 14, 2026 | Eugene, OR | 6K, 4K, 1M | More Information |
| 5K Fun Run/Walk Senior Project | May 16, 2026 | Hillsboro, OR | 5K | More Information |
| Brave Run | May 16, 2026 | Banks, OR | 10K, 5K | More Information |
| Canby 5K/10K | May 16, 2026 | Canby, OR | 10K, 5K | More Information |
| Crush Cancer Run | May 16, 2026 | Terrebonne, OR | Half Marathon, 10K, 5K | More Information |
| Dirty Pelican Bike Paddle Run | May 16, 2026 | Klamath Falls, OR | Sprint Triathlon, 5K | More Information |
| Happy Valley Fun Run | May 16, 2026 | Happy Valley, OR | 10K, 5K | More Information |
| Maupin Daze 5K/10K | May 16, 2026 | Maupin, OR | 10K, 5K | More Information |
| Miles for Midwives | May 16, 2026 | Saint Paul, OR | 5K | More Information |
| Oregon Cattlewomen Ranch Run | May 16, 2026 | Klamath Falls, OR | Half Marathon, 10K, 5K, 1M | More Information |
| Pole Pedal Paddle | May 16, 2026 | Bend, OR | Olympic Triathlon | More Information |
| Rhody Run | May 16, 2026 | Florence, OR | 10K, 5K | More Information |
| Run 2 Remember | May 16, 2026 | Salem, OR | 5K | More Information |
| Tillamook Burn Trail Run | May 16 & 17, 2026 | Timber, OR | 50M, 55K | More Information |
| Tough as Nails | May 16, 2026 | Medford, OR | 10M, 5K | More Information |
| Oregon Brewery Running Series – Trap Door | May 16, 2026 | Vancouver, WA | 5K | More Information |
| Wood You Rather | May 16, 2026 | Portland, OR | 8M | More Information |
| Bark in the Park | May 17, 2026 | Eugene, OR | 10K, 5K, 2K | More Information |
| Cottage Grove Half Marathon | May 17, 2026 | Cottage Grove, OR | Half Marathon, 10K | More Information |
| Reflection Run | May 17, 2026 | Washougal, WA | 13.1M, 10K, 5K | More Information |
| KeizerFEST 5K | May 17, 2026 | Keizer, OR | 5K | More Information |
| COCC Storm the Stairs | May 19, 2026 | Bend, OR | Stair Climb | More Information |
| Portland Trail Series – Spring | May 20, 2026 | Portland, OR | 6M, 4M | More Information |
| Emerald City Trail Series | May 21, 2026 | Eugene, OR | 4.7M | More Information |
| Eastern Oregon Half Marathon | May 23, 2026 | Spray, OR | Half Marathon, 10K, 5K | More Information |
| Hillsboro Hustle 5K | May 23, 2026 | Hillsboro, OR | 5K | More Information |
| Hurricane Creek Half Marathon | May 23, 2026 | Joseph, OR | Half Marathon, 5M, 5K | More Information |
| Oregon Trail Game 5K | May 23, 2026 | Oregon City, OR | 5K, Kids Run | More Information |
| Ridgeline Ramble | May 23, 2026 | Eugene, OR | 20K, 10K | More Information |
| Stumptown Trail Runs | May 23-25, 2026 | Portland, OR | Half Marathon | More Information |
| Miles on Memorial | May 25, 2026 | Eugene, OR | 15K, 10K, 5K, 15K Relay | More Information |
| Run the Couve Series | May 28, 2026 | Vancouver, WA | 5k | More Information |
| Rose Festival Street Mile | May 30, 2026 | Portland, OR | 1M | More Information |
| Oregon Brewery Running Series – Gorges | May 30, 2026 | Cascade Locks, OR | 5K | More Information |
| Oregon Tech Twilight Fun Run | May 30, 2026 | Klamath Falls, OR | 5K | More Information |
| Rose Festival Street Mile | May 30, 2026 | Portland, OR | 1M | More Information |
| Run On The River | May 30, 2026 | Astoria, OR | Half Marathon, 10K, 5K | More Information |
| Skyview Falcon 5K/Mile Adventure Run | May 30, 2026 | Bend, OR | 5K, 1M Adventure Run | More Information |
| Smith Rock Classic | May 30, 2026 | Terrebonne, OR | 50M, 50K, 10M | More Information |
| Sole Sisters Half Marathon | May 30, 2026 | Wilsonville, OR | Half Marathon, 10K, 5K | More Information |
| YRun Dayton 5K | May 30, 2026 | Dayton, OR | 5K, 1M | More Information |
| Newport Marathon | May 31, 2026 | Newport, OR | Marathon, Half Marathon | More Information |
| Oregon Wine Country Half Marathon | May 31, 2026 | Dayton, OR | Half Marathon, 5K, Relay | More Information |
| PDX Triathlon Festival | May 31, 2026 | Fairview, OR | Triathlon, 5K | More Information |
