Portland, Oregon · Saturday, September 12, 2026
The PDX 50-50 is a 50k and ultra event held on Saturday, September 12, 2026. It is located at 3400 SE Milwaukie Ave in Portland, Oregon.
Welcome to the third annual Milwaukie Mile! Our goal is to provide a safe and fast course for all members of the community to race their pace and set a new personal best in the mile! The course runs gently downhill along the Trolley Trail, starting at the Park Avenue Max Station and finishing in Milwaukie Bay Park. The race will be held the morning of Saturday July 11th, 2026.
The race is open to runners, walkers, and families with strollers. Dogs are not allowed to accompany runners, walkers, or volunteers. You can spectate with your dog on a leash, but please stand back from the course when doing so for the safety of the participants.
Please note - T-shirt size and availability are not guaranteed for registrations after July 1st.
Awards
All registered participants will receive a Milwaukie Mile T-shirt. The top-3 finishers in the following categories will receive a special award:
Non-binary
Open Women
Open Men
18 and under Girls
18 and under Boys
Transportation
The race starts only a few steps from the Park Ave Orange Line Max Station. Participants and spectators are encouraged to use public transportation to travel to the race! If you must drive to the race, auto users are encouraged to park in Downtown Milwaukie or at the Park Ave park and ride garage
Donations
A portion of the race proceeds will be donated to the Milwaukie High School Cross Country team. If you want to make a dedicated donation to the team to support their 2026 season, we will gladly pass 100% of your donation on to the team! Any amount given would be greatly appreciated and thank you for your generosity! Please click the Donate tab above to donate directly.
Sponsorship
The Milwaukie Mile is a small community event which would not be possible without the support of generous sponsors. If you would like to support or sponsor the event in any way, please email [email protected].
Volunteers
Milwaukie Mile is supported 100% by some amazing volunteers! They help us with event coordination, athlete safety, and logistics. If you would like to volunteer, please email [email protected].
Photos:
Mateo Flores was out on the course capturing all the fun in 2025. Photos can be found on a shared google drive linked HERE. These are free for you to download for personal use - we only ask that you honor Mateo’s hard work and give photo credit to Mateo Flores or tag @teotooktheflick when sharing on Instagram. Feel free to also tag @milwaukiemile so we can celebrate with you!
What Is OUTLAST?
OUTLAST is a 6-hour trail endurance challenge where runners complete a 5K every hour, on the hour. Each lap must be finished within the hour to stay in the event. If you finish early, you rest until the next round. Miss a lap, and you’re out.
Complete all six rounds, and you OUTLAST.
This isn't just about speed — it's about pacing, discipline, and mental grit. Whether you're trying to survive all six or win your division, the challenge is the same: show up each hour, push your limits, and stay in it.
Each course is trail-based, with natural terrain, elevation, and unpredictable conditions. You’ll have time between rounds to recover, refuel, and refocus — but not much.
What You Earn:
4 laps = “Grit Earned” patch
5 laps = “Survivor” patch
6 laps = Premium “OUTLAST” medal
All participants receive a premium OUTLAST Tee.
Top male and female with the fastest combined 5K times at each event win the 1st Place OUTLAST award.
Finishers are ranked on the national leaderboard—and the fastest runner across all OUTLAST 6-hour events will be crowned National Champion and take home $1,000.
The 1st Place Male and Female 6-hour champions from each city will earn a spot in the Outlast Championship, where they’ll compete against the best of the best at the end of the Tour, and the 1st place male and female winners take home $1000 each. (This is separate from the national leaderboard prize money.)
By the end of the tour, the top 100 best times nationally will be invited to also compete in the Outlast Championship.
Frequently Asked Questions:
Do I have to run all 6 laps?
Nope. Run as many as you can. If you complete 4 or 5, you'll still earn a patch. Only those who finish all 6 get the OUTLAST medal and leaderboard ranking.
What happens if I don’t finish a lap in time?
You're out. The next lap starts at the top of the next hour, and only those who completed the last lap on time can continue.
How is the race timed?
Each 5K is timed individually. If you complete all 6, your combined time counts toward the local win and national leaderboard.
Are these trail races or road?
Every OUTLAST race is on trail terrain — dirt, rocks, roots, and elevation. Sometimes some pavement and gravel.
Can I walk?
Yes, as long as you finish the 5K within the hour. But some courses are rugged, and time can sneak up on you.
Are there aid stations?
Yes. There will be water, basic hydration, and snacks at the basecamp/loop start. This is a cupless event — bring your own bottle or hydration system.
What should I bring?
Trail shoes, hydration system, layers (weather dependent), fuel between laps, and grit.
Can I setup a tent?
Absolutely, bring your own aid station/tent setup.
Is OUTLAST for beginners?
Yes — if you're mentally tough. You don’t need to be fast, just consistent and ready to suffer a little.
How do I win?
If you finish all 6 laps and have the fastest combined time, you win your division (male/female). Winners are also added to the national leaderboard for a shot at the $1,000 national prize & title.
Step into your favorite character’s shoes—whether you’re a superhero, anti-hero, villain, knight, princess, or even Sasquatch—and join us for the inaugural Dragonslayer Fantasy Dash & Strut!
This 5K adventure invites you to walk or run through the magical trails of Gabriel Park (PDX). Along the way, you’ll encounter a thrilling Villain Zones for an extra dash of fun and excitement and be welcomed back to the Heroes Village!
Route includes mild inclines, a mixture of gravel and trail pathways, everyone is assured of a beautiful and accessible run, jog, or walk. The route is suitable for all ages and abilities. Leashed dogs and strollers welcome (strollers ensure you have wheels suitable for unpaved trails).
Lace up your sneakers, gather your squad, and head out for a day of fantasy, fitness, and unforgettable shenanigans. Costumes encouraged; laughter guaranteed!
Ready to hit the streets of Oregon for the famous Portland Marathon 🌟? Whether you're a fan of the 10K run or ready to tackle the challenge of the marathon, this race is perfect for you!
Jacuzzi Boys Athletic Club launched in Portland, Oregon in 2014, built around three ideals: work hard, enjoy the experience, and never miss the forest for the trees. The crew believes that performance matters, but so does presence, running with ambition and awareness while keeping the experience itself as the whole point. Members hail from across the country, though Portland remains home base, where the vibe is genuine and the effort is real. From Forest Park's Wildwood Trail to the city's iconic river bridges, Jacuzzi Boys Athletic Club runs with curiosity, grit, and heart, proving that the company you keep makes every mile worth it.
Stumprunners began in Portland's heart in November 2012, when four friends decided that trails belonged in their weekly routine. They wanted to run among the city's ancient trees, connect with each other, and build something that lasted. Today, around 30 runners of all levels gather every Saturday morning at Dragonfly Coffee House before heading into Forest Park to tackle the Wildwood and Leif Erikson trails. The crew runs for the trees, the trails, and each other, with social connection and mutual support woven into everything they do. Post-run plates and pints are part of the deal, too.