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Portland: Our insider’s guide to running Rose City

Nestled between the Pacific Ocean and the Cascade Range, Portland has introduced itself to the surrounding nature by becoming a part of it. Enveloped by deep forest, generously lined with flourishing parks and gently divided by the Willamette River, one could say Portland is at one with its environment. But let’s put this statement to the test by, you guessed it, running through it.


Once home to a humming industrial port and thriving logging industry, Portland has transformed into one of the greenest cities in the US. And this nature-friendly approach has been imprinted on city planning. The result? Plenty of space to relax, stroll or run.


Just visit one of the many inviting parks scattered throughout Portland and feel the city blooming around you. Or, maybe, head downtown and indulge in the local culinary landscape – after your run, of course.


But for now, let’s stay on our feet and focus on what we’re here for, exploring a new city. And this usually works best if you have someone to show you around. Luckily, we know just the guy. He’s got three routes to show us, so tag along and find out what makes running in Portland so worth trying. 



Meet your guide


Our guide and On Run Crew member Rajiv is no stranger to the Portland running scene. He does what he can to lead a healthy lifestyle, focusing on training and nutrition and helping to empower others to do the same.


“I was born and raised right here in Portland. It’s the place I’ve always called home,” says Rajiv. 


“My favorite thing about it is that it’s a very health-conscious city, where activity and adventure are easily accessible and encouraged.”


“Today, I’m a health and wellness coach, a plant-based chef and a community builder with a mission to help others embrace a healthier existence.” 



Meditation on the move


Rajiv has welcomed running to his life. And to open this door for others as well, he founded the Embrace Change Run Club. Holding regular meetings at Waterfront Park, he strives to provide a safe environment for anyone willing to sweat.


“Running has become my peace. For me, it’s a positive outlet to be free to move my body and mind positively.” 


“It’s a space to become more grounded, move your body in a healthy way, a space to connect and to be encouraged. It’s been in my heart for some time to continue building community and awareness in Portland through running.” 


“Running isn’t just exercise to me. It’s my meditation.” 



5KM – Waterfront Loop


We meet Rajiv for a quick 5KM at the Japanese American Historical Plaza, surrounded by cherry blossoms in the spring. This route draws a crowd for a couple of good reasons. The first being the beautiful views you get along the Willamette River. Another being the lively atmosphere created by fellow athletes, families and visitors to the Saturday Market – which is a great option to refuel after a weekend run. Rajiv likes this route so much that he regularly takes his running club on this 5KM loop to feed off the energy it exudes.


“Whether you’re visiting from out of town or on lunch break, this beautiful 5KM route on the waterfront is a must – if only to enjoy the panoramic views of the city from both sides of the water!”


5KM – Waterfront Loop
See on Strava
10KM – Rose Garden Loop
See on Strava


10KM – Rose Garden Loop


Ready to take things up a notch? Let’s increase the distance and throw in some elevation as well. We hope you’re just as excited for this as Rajiv, who’s waiting for us at Wallace Park. Make sure you save some energy on the flat start through the Alphabet District because before too long, you’ll pass the magnificent International Rose Test Garden and start your climb up the nearby trails. Side note: it’s impossible to get lost in the Alphabet District because all street names are in alphabetical order – cool, right? 


Running past the incredible views from Pittock Mansion, you’ll realize just how extensive the trails of Portland are. In fact, the city is home to the largest network of trails within city limits in the US. For the most part, these trails are well maintained and can be tackled without special trail running shoes – though we have some recommendations for you if you’d like a pair.


“I love this route because you can escape the city limits without traveling far. Out here, you’ll get to experience Portland’s lush green forest and trails.”


Need to fill up on energy at the beginning or end of this loop? Make sure to stop at Dragonfly Coffee House for a coffee and pastry or Moberi for an açai bowl or smoothie.


How to start trail running: A beginner’s guide
Learn more


15KM – South Waterfront Loop


We’re back at the starting point of our 5KM route, but let’s pump that distance up to 15KM. Starting in the heart of Portland, the urban waterfront quickly turns into a not-so-urban waterfront. But that’s what we want for this route. Before you know it, you’ll be able to focus solely on your run – no shops, no cars, just the road ahead. Since the route runs relatively flat with plenty of straight sections, it’s welcoming to anyone who wants to do some speed work or to relax and switch off.


If the heat is catching up to you, consider taking a dip in the Willamette River. Otherwise, you might at least get some cool thoughts while taking in the views of snow-covered mountain tops.


“Portland isn’t called the “Bridge City” for nothing.” 


“On this route, you’ll cross two of Portland’s nicest bridges, perfectly outfitted for runners. Lock-in, get focused, and turn up the speed on this mostly flat route.”


After this challenging but revitalizing trip through Portland, a vitamin-packed smoothie at Green Leaf is well-deserved. Also, don’t miss the breakfast at Little River Cafe to cap off your successful run.


15KM – South Waterfront Loop
See on Strava


Running tips


- Keep your eyes peeled for breathtaking views of Mt. Hood and St. Helens in the distance

- Don’t fear the rain – embrace it

- Take a moment to pause, reflect and give thanks for your practice

- Play nicely with cyclists; there’s enough room for us all

- Throw up a peace sign or exchange a smile with your fellow run community


Rajiv’s wearing

Cloudswift – Conquer concrete
Light and swift with impact protection. Features Helion™ superfoam so running on hard surfaces never felt easier.
Weather Jacket – Weightless weatherproofing
The running jacket for ultralight protection, whatever the weather. Made with high-tech Japanese fabrics, it’s the perfect companion for wild runs.
Weather Jacket
High Sock – Sock on, stand out
The standout performance running sock that always has you covered. A statement of intent for your run.
High Sock
Performance-T – The podium-topping top
The performance running T-shirt for racing. Reduced to the max, it balances ultralight protection with breathability and freedom.
Lightweight shorts – As fast as light
Ultralight, versatile shorts with a perforated back.
Lightweight shorts

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