Lovejoy to Skyline Loop – Portland, OR

The essential key to great rides in the Portland metro area is knowing how to navigate the West Hills. They dominate the skyline west of the city; providing great views and a lot of great rides, if you know how to traverse through them.

My first experiences riding in Portland were incredibly frustrating. I could see the hills that I wanted desperately to climb, but for the life of me I could not figure out how to get into for any sort of meaningful ride. Stubbornly, I would set out from my house with map in hand, only to become frustrated at the changing road names, the narrow streets that dead ended suddenly and the increasingly irate drivers who seemed to recognize the overly large cyclist with his too-tight spandex (it IS actually possible to have spandex that is too tight). Eventually I broke down and asked one of the TAs at school, who was a cyclist, what he recommended. His first inclination was to send me up NW Lovejoy in order to orient me with Skyline Boulevard.

Lovejoy runs from East to West, in the Northwest section of Portland. After rolling through the trendy Northwest part of the city, the road heads into the Forest Park area of the Hills. Lovejoy provides one of the closest and widest routes into the West Hills. There are two tunnels along the route; with paved paths that detour around them so you don’t have to share the tunnels with cars. As the road continues to climb I always take a right on NW 53rd Drive (its basically the first real road that you come across as you climb). 53rd Drive is a beast in and of itself. It starts steep and stays steep for a good mile before leveling out. I often use this road for hill sprints – it is one of the better and more quickly reached climbs in the West Hills. 53rd Drive will eventually fun into Thompson, which climbs up to Skyline Boulevard. From this point, you can head North (by taking a right) or South (a left). For this loop, I head left and take Skyline to where it intersections with Cornell and take a left for an incredibly fast descent. On the downhill I forgo the diversions around the tunnels. Just keep an eye out for potholes.

I love this ride for a couple of reasons. Mainly its close; it is really easy to access from downtown Portland and makes for a great after work/before dinner ride. It’s also short enough to not get in the way of the rest of the day, but has enough climbing to provide for a great workout. It also has some great views of the Cascades, and rolls by some incredible houses. Lastly, this loop is a great basis for other rides in the area, and can serve as a great warmup to some more intense cycling.

Distance: 11 miles roundtrip

Time: 45 minutes on average

Directions: start at 10th and Lovejoy and head West on Lovejoy (it has a bike lane for some of it, but once that ends the road is wide enough to not be too much of a problem). The road with head through the Northwest neighborhood and climb briefly up to Cornell (which Lovejoy turns into). Bear right and head past some gigantic houses. The road will climb slightly before veering right and beginning a gradual climb that winds through the two tunnels. At NW 53rd Drive take a right, and follow that until it runs into Thompson. At the stop sign turn right where the road climbs up to Skyline. Take a left at the stop sign and follow Skyline back to Cornell. Left at the stop sign for a screaming descent back down.


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