Roads Like These: Vol. 3 // NW Hills of Portland, OR

Photos by Jake Szymanski // Words by Alex Dickinson


We may not have mountains in our backyard here in Portland, but if you’re riding close to the city you’re going to be doing some climbing. That’s mostly due to the West Hills, the well-renowned territory knit by Skyline Boulevard, which is much of the reason riding in Portland is so damn good. We chose ten of our favorite climbs across the northwest section and photos from throughout the season to tell a story about each one.

1. Dixie Mountain

One of the best rides I’ve ever been on was with about 12 or 15 people, on a Saturday morning in early spring. Before the ride, I knew maybe 2 of these gents, but as we rolled out the chatter was loud and the excitement for the approaching season was palpable.

We settled on Dixie Mountain for the route, and the pace stayed conversational until we hit the long gravel climb. When a couple of mountain goats went off the front, Pete Rubijono and Dan Sharp, I followed. We rode that thing so hard, testing each other the entire way up, digging deep and breathing hard. Couldn’t think of a better way to make new friends.

2. Moreland Dorland

One of the best climbs in Oregon, period. There’s also a guy that drives this road a lot in a big white SUV, flipping cyclists off unprovoked, but he’s mostly harmless.

3. Newberry

A tip from a good friend and local legend: attack it really hard at the beginning. “Get it over and done with. It mellows out after this,” he says. Not true. The 10% grade on the first couple switchbacks lets up for a moment, but that’s it. It’s a beautiful road, but going full gas from the start is ill advised.

4. Springville

“Want to go down Springville?” is a question I’ve never said no to. It’s the one on this list I definitely think of as a descent. Ripping down this thing is my favorite early morning ritual, with the cold wind in my face, scaring myself just a bit on the long, sweeping corners. On the best days, you’ll descend until you’re completely enveloped in a blanket of fog that sits on the North Plains.

5. Mt. Munson

With current trends in cycling and menswear in general, one might guess this road got its colloquial name, Peacocks, from a showing of manly flamboyance. The first time I rode it, unaware of the name and ripping down a gravel descent, I heard squalls in the distance and thought some Jungle Book, baby-in-the-woods shit was happening. Rounding a hard left, I was greeted by one of the large birds and his plumage. Never has anything looked so out of place.

6. 53rd

This climb doesn’t lie. It’s quick but super steep and it’ll let you know how you’re feeling in a hurry. Portlanders love it for light traffic and views of Forest Park and the Wildwood Trail, but they respect it, too.

7. Old Germantown

I passed by this road about a hundred times without knowing it was there when I moved to Portland. When Jake showed me the slight right off (new) Germantown to Old Germantown, I couldn’t believe it. It’s truly a hidden gem and somewhat of a right of passage for riders in the area.

8. Rock Creek

There’s something a bit sad about Rock Creek. The cycling is perfect. There’s a really pretty climb and views of the Oregon countryside and there’s hardly anyone out there, but the country road is lined with weird little houses, barns, and cabins, none of which try to be quaint or idyllic. The decrepit structures are the antithesis of storybook cottages. I’ve heard gunshots nearby multiple times. I always have a good ride on Rock Creek, but it never fails to remind me what a sheltered little world we live in just a few miles away in Portland.

9. Saltzman

Saltzman Road is the only climb on this list that goes directly through Portland’s famous Forest Park, so it’s the best way to get up into the hills when the traffic gets bad. The gravel one-laner is shared with hikers, runners, and their dogs. When you see the gate, sprint!

10. McNamee

A friend of mine rode McNamee for the first time a while back. He was climbing pretty hard, and about half way up, he thought he was starting to hallucinate. The climb is seriously steep and about half way up, a trestle is decorated with several trolls, both dolls and painted figures. No one really knows the origin of the tradition, which adds to the creepiness. For cyclists, they’re good for a much-needed laugh when you’re battling the steep grades.