Wildwood Adventure Days
Have you always wanted to run the full length of Portland’s legendary Wildwood Trail but didn’t want to do it alone or deal with the logistics? Or maybe you’re more inspired to support people running it? Or maybe want to spend the day in forest park walking or running just sections of the Wildwood trail?
Whatever your journey is, this is your chance. Join a crew of like-hearted trail lovers for a fully supported, community-powered point-to-point adventure through Forest Park, capped off with an epic trailgating celebration.
Whether you’re tackling the whole trail or jumping in for a few sections, we’ve got you covered. Your entry includes shuttle support, aid stations stocked with hydration, nutrition, and first aid, plus all the good vibes waiting at the finish line.
Trail + Art
For those of you who aren’t running the full 30 miles, you might be wondering what the day looks like while we wait for our runners. Obviously, we drink coffee, eat delicious food, listen to music, and cheer like crazy, but we also get creative.
We’re introducing an art box. Being in nature is one of the best times to tap into your creativity, so we’re supplying all kinds of mediums to play with: watercolors, pastels, pens, pencils, and all kinds of paper.
Whether you sketch the moss on a tree, watercolor the morning light, or just doodle your trail feelings, we can’t wait to see what you create out there.
The Afterparty: Blue Diamond Pizza
At the finish, the celebration continues with Blue Diamond Pizza, a mobile pizza business founded by fellow trail runner and food lover, Josh Casey.
The ethos says it all:
Being a heartfelt gathering place where the simple act of sharing a slice strengthens opportunity for community. We’re dedicated to crafting exceptional pizza that nourishes both body and spirit, making us a beloved part of connections, trials, and deliciously good times.
The name “Blue Diamond” nods to the very markers that will guide you all day, a symbol of connection, direction, and the spirit of the trail itself.
The menu will be vegan-friendly, and if you have any other dietary restrictions, just let us know ahead of time and we’ll make sure you’re covered!
Who: All skill levels welcome
Run Options:
Advanced: Go all in—30 miles of uninterrupted Forest Park magic.
Intermediate: We’ll help you choose your own adventure with guided entry/exit points based on your fitness and vibe.
Cheer Squad: Want to be part of the energy without running? Ride along in the van and cheer on runners at aid stops and the finish line.
FAQs
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It depends on your pace, trail conditions, and how often you stop. Speedy runners can finish in as little as 5.5 hours. Most folks land somewhere between 6–9 hours. We’ll help you plan the timing that works best for you and your crew.
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You’ll need the basics: trail shoes, a hydration pack or bottles, nutrition, layers, and a charged phone. After your consult, we’ll send you a suggested gear checklist based on your route, pace, and the forecast. We’ve got you covered.
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It happens! We keep a stash of backup gear and clothing (men’s and women’s options) just in case. If you realize you're missing something essential—hydration pack, extra socks, you name it—let us know as early as possible and we’ll do our best to help.
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Only a couple! There’s one flushing toilet at Pittock Mansion and two porta-potties near the south end. The rest of the time, you’ll be doing your business in the woods. If this is new territory for you, don’t stress—we’re happy to walk you through what that looks like. We’re not afraid to talk about poop.
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North to South (Newberry to the Zoo): ~3,300 ft gain
South to North (The Zoo to Newberry): ~3,000 ft gain
We’ll help you decide which direction suits your goals, vibe, and legs best.
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No problem at all. We’ve supported runners, hikers, and everything in between. You don’t have to move fast—or even cover the full 30 miles—to have a meaningful experience. Our shuttle and aid support make it easy to adjust your plan mid-run if your body (or brain) needs a break. This isn’t about perfection—it’s about showing up, moving forward, and soaking in the journey at your own pace.
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We’ve got you covered with simple, nourishing options designed to keep you fueled and feeling good. Aid stations will include hydration, salty snacks, sweet bites, and real food when possible—all chosen with active bodies in mind. After the run, we’ll celebrate with a casual tailgate spread featuring Sizzle Pie pizza (including vegan and gluten-free options), drinks, and recovery-friendly snacks. If you have specific dietary needs or sensitivities, just let us know—we’re happy to accommodate.
This special Wildwood Adventure Day celebrates Annalou’s 7 years alcohol-free and the power of community in motion. Proceeds from this event support the Portland Alano Club, helping fund programs like RUN TRG and the Recovery Gym, which create access to movement, connection, and sobriety support. Come run, hike, cheer, or volunteer, and be part of something bigger than the miles. Secure your spot!
How the fundraiser edition works
Secure your spot for the day by adding to the cart and checking out. This way we can make sure we have enough seats in the shuttle and food for the aid stations and after party!
Please consider donating with the link below.
You don’t need to be in or seeking recovery to participate in this event, just believe in the cause. Programs like RUN TRG and the Recovery Gym save lives!
Join us for a fully supported, point-to-point run of Portland’s legendary Wildwood Trail.
Includes shuttle service, aid stations with hydration + nutrition, and an afterparty with pizza, drinks, and community vibes.
All paces welcome, run the full 30 or hop in for a section.