Hiking the 30-mile Wildwood trail

Before you think I’m crazy for wanting to hike 30 miles, I would like to point out how many people run marathons. That’s 26 miles running so while hiking 30 miles sounds intense, there is zero running involved*.

Now that we’ve gotten that out of the way, let’s talk about the 30.5 mile Wildwood trail here in Portland:

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That’s right – here within city limits you can hike 30 miles if you so please. I’ve always wondered if I had it in me, and how challenging it would really be so that is how this goal landed on my bucket list for 2017.

The first real challenge was finding someone stupid willing enough to join me, as most people just gave me a goggle-eyed expression about hiking 30 miles. Lucky for me, my bff, Courtney, was up for the challenge. While both of us have hiking experience (who doesn’t in Portland?) and we both exercise frequently, hiking isn’t exactly on our regular radar.

Step 1:

We decided that we would parse out a few longer hikes on the route before taking the 30 mile challenge, starting with a 14-mile hike. I mostly referenced this article from OPB Hiking Portland’s Wildwood Trail in 5 Partsiking Portland’s Wildwood Trail in 5 Parts, knowing that we would want to end our trek at Skyline Tavern for post-hike beers.

Our 14-mile hike went extremely well, starting at the Forest Lane/NW 53rd Dr entrance and ending near Germantown at Waterline & Skyline. We did stop and look at the map many times (as cell service is iffy, and many smaller trails intersect Wildwood), and Courtney saved many slugs on the path, so our pacing wasn’t exactly vigorous. At the end of the hike, my feet hurt a bit, but I certainly felt that I could extend my mileage a bit.

Step 2:

Riding high on our first experiment, we decided our next hike should be around 20-22 miles. I scrutinized the map carefully, knowing that any wrong turns would cause us extra steps we would regret later on. There were a lot of things to consider: how long would it take us? what should we bring? what is the best footwear? what if we decide to bail early? who will pick us up? what if there are bears? We coordinated our attack – I brought sandwiches, Courtney brought pepper spray.

Our most important items were good footwear, a lot of water, snacks, bug spray, toilet paper, and an external charger for our cell phones. OH, and my new Apple Watch, which would accurately track our mileage the whole way.

Step 3:

Knowing our pace was questionable steady, we set out at 6:30am and parked where Wildwood meets Burnside, below the Pittock Mansion (very bottom right on the map below):

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Unfortunately, just a mile in, the damned Wildwood trail was closed due to a landslide! There was a confusing detour that led us through the neighborhoods of Northwest Portland and back onto the trail near Cumberland.

Proverbial scenic shot from the Pittock Mansion viewpoint (1.5 miles already in)

Following the trail was sometimes confusing, and for as much as I could look at the map that seemed clear, when you’re actually in the woods and someone has ripped the sign down, it’s less easy. But we did pretty well – going at a comfortable pace, stopping periodically to rest our feet and have a snack.

Courtney has an intense fear of bears (whereas I have an intense fear of bees), and we joked that if I saw any signs of bears I would alert her rather than let her hike unaware of danger. Somewhere around 10 miles in we ran across this:


A fresh pile of bear scat, that we quickly cross-referenced on Google for confirmation. We decided to have a very loud conversation about the new Game of Thrones episode and moved on quickly.

At 16 miles, our feet started to hurt. Not terribly, but enough to notice. At 18 miles, it got more intense, and I continued to scrutinize the maps to make sure we were on the right track. At 18.5 my Apple Watch died.

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Nonetheless, we kept on going and made it. We finished where Waterline & NW Skyline meet. Although my watch died, I’m pretty positive we met our goal. Total time: 8.5 hours and we celebrated at Skyline Tavern with a pitcher of beer.

Now What?

I’m not sure we are committed to the full 30 miles. Yesterday was hard, and I think we could do it again – but a full 30? My feet might revolt.

I do fully intend to finish the other part of the trail we have yet to cover, from Germantown to Newberry.

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Courtney and I agreed that an 8 or 9 mile hike sounds like a baby hike – we could do that in our sleep – so what comes next is up in the air. We like a challenge, but we don’t want to die.


It is now very clear to me why I would never run a marathon. I run a lot, I can hike a long distance, but running a marathon sounds like another circle of hell.

How do you marathoners train your feet to not hurt?!



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