A Runner’s Guide to Portland

by Fitt
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A Runner’s Guide to Portland

San Diego has its beaches, Chicago has the lake and New York City has Central Park. But Portland has to be one of the best running cities around thanks to a near perfect mix of friendly city streets and stunning trails. On any given day, there’s someone to run with and an amazing brunch spot waiting at the end.


From city streets to off-road trails and tree-lined paths, Portland has a route for every kind of runner.


Running along the waterfront is like a choose-your-own-adventure story. It depends on how far you want to go — pro tip: Just pick a bridge! For a fantastic 11-mile jaunt with excellent views of the Willamette River and Portland skyline, start at the Steel Bridge on the north side of PDX, traverse the Eastbank Esplanade and cross back at the Sellwood Bridge. Or you can easily shorten the route with the Hawthorne Bridge or Tilikum Crossing.


There’s no better sound than the audible crunch of a run on Leif Erikson Drive. It’s a 12-mile out-and-back route you’ll never tire of. The gravel fireroad is well-maintained, and couldn’t be more PNW: ferns, mossy trees and a number of mud-flinging bike tires. Don’t let that deter you, though. There’s plenty of room for all, and also a number of opportunities to sneak over to the more rugged Wildwood Trail.


Oh, and that Wildwood Trail — it’s your ticket to some Portland sightseeing, trail-run style. Start in Macleay Park, and set out on the Lower Macleay Trail. You’ll soon find yourself at the Witch’s Castle. More formally called the Stone House, the abandoned structure really does look haunted. Once you’ve had your photo, continue up the fairly steep, frequently muddy Wildwood Trail. You’ll traverse a few switchbacks before appearing in the parking lot of the exquisite Pittock Mansion. Just don’t expect to be admitted to the marbled foyer in those muddy kicks.


Terwilliger Boulevard has a lot to offer runners: a wide sidewalk, quad-hammering hills and a perfect mix of tree canopy for shade and street lights for evening runs. If you park at the Duniway Track, you can work your way up to an epic view of the river, the city and, if you time it for sunrise or sunset, a pink or orange Mount Hood in the distance. It’s no surprise Terwilliger is the literal stomping grounds for tons of Portland runners. It’s also right in the shadow of Under Armour’s gleaming new Portland campus, which overlooks the Duniway Track.


Because running in Portland is always better when there’s someone to point weird things out to. #KeepPortlandWeird


Photo Credit: Oregon Road Runners Club

If you believe in strength in numbers, ORRC’s community, races and weekly group runs will certainly win you over. Running throughout the week, these open runs bring out novice and veteran pavement-pounders alike. And you know, the Pizza Runs every first Thursday of the month really want to make us run.


This outfit offers even more opportunities to run throughout the week. Actually, every day of the week except Friday. Their expert guidance and instruction will make you a better runner in no time. And if you’re one who gets bored with running, meet your new best friends. They’ve got short runs, long runs, trail runs, track runs and even Rogue runs. Yup, Thirsty Thursdays end at Rogue Eastside Pub & Pilot Brewery, where the first one is on the house!


Everyone smiles here, but they’re serious about their training. Their marathon, half-marathon and offseason training are designed to help runners of all abilities complete and dominate signature Oregon races like the Portland Marathon and Half-Marathon, the Helvetia Half-Marathon, Hood to Coast and many more.


Whether you’re prepping for a long run or patting yourself on the back after some Portland hills (more like patting a full belly!), PDX certainly delivers.


Photo Credit: Harlow Restaurant

This cozy joint in Southeast Portland embodies everything we could ever want in a healthy eatery. It’s  all about “fresh, conscious cuisine,” so you know its sourcing is all-Oregon, all-delicious. The staff uses those fresh ingredients to create unbelievably tantalizing vegan, vegetarian and gluten-free creations. It  serves breakfast, lunch and dinner, but we’ll meet you at brunch time for unbelieveable bowls, scrambles and the magical feast of Harlow Rancheros.


If you need something light before a run, juice makes all the sense in the world. Setting up in a converted camper in Southeast Portland and a second cart on NE Alberta Street, Sip Juice Cart promises only the most flavorful, organic juices. Stick with something safe like the sweet green juice or put a little pep in your step with a 2-ounce master shot of ginger, lemon and cayenne pepper. If you’re going to try to tackle the Sellwood Bridge Loop, however, the almond bowl would sit right given 30 minutes to digest.


If you need something to celebrate that run, there’s no better spot to do so than the ginormous patio here. It serves food for all omnivores, but really does vegan and vegetarian food the best. Snag an order of buffalo cauliflower wings and kick back on the dog-friendly patio with a strong adult beverage (they’re heavy-handed on “the sauce”) for the perfect post-run cool-down. Fitt tip: Definitely hydrate before the round of cocktails.


Whether you’re running for fun, a PR or beer a cold Portland brew, Portland has year-round races you need on your calendar.


Want an express tour of Oregon? Gather 11 of your friends and rent a van for the mother of all Portland running feats (with your feet). The Hood to Coast Relay goes down every August over two days of running. Starting at the base of the magnificent eponymous Mount Hood, you’ll traverse 200 miles over two days through mountain, forest, urban jungle and end at the beach in Seaside. By the end, you’ll love your running family more than your actual family. Registration for this year’s event is closed, but you can still cheer runners along the course August 25–26, 2017.


How many more of our favorite things can you put into one race? You’ve obviously got the whole running thing, but also Oregon countryside, a pint from Full Sail Brewing, post-race pasta feast — it goes on. And the race — run from the starting point at the Hood River County Fairgrounds to the small riverside town of Hood River — presents an excellent opportunity to hit your PR. Maybe because it’s mostly downhill, but probably moreso because you have noodles and beer waiting for you at the finish. September 24, 2017.


Photo Credit: Portland Marathon

This one is consistently ranked among the top marathons in the country. You’ll never be bored during your run — climbing the bluff on the East Side for beautiful views and crossing the iconic St. John’s Bridge will keep you occupied. Not only that, but the portion of your 26.2 through downtown Portland is lined by countless jammin’ bands and tons of onlookers cheering you on. Add in perfect race temps (usually around 52 at the starting line) and totally PNW swag (a Portland rose and a tree seedling to plant in your yard). The only bad things you’ll have to contend with are the Jell-O legs of miles 20–26. October 8, 2017.


Just one of the many events of the famous Portland Rose Festival, the Starlight Run has preceded the famous Starlight Parade for 40 years. And it’s a heck of a lot of fun. Runners are encouraged to dress in costume and party in the streets along the 5K route of this summer evening race. Stick around for the Starlight Parade afterward, with plenty of glow-in-the-dark fun and a live DJ. June 2, 2018.

About the Author

Fitt is the go-to resource for connecting with your local fitness community. Fitt’s contributor network is on the ground in cities across the country to help you discover the best workout spots, healthy eats, outdoor adventures and upcoming events near you. Head to Fitt.co to see if we’re live in your city. Be sure to follow along on Facebook and Instagram for the latest updates.


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