On the first Portland rainy day of the hike, we left the Sunnyside neighborhood and headed to the northern Mt. Tabor area to hit up some neighborhood stairs that we didn’t catch on the day we walked through the park. My friend So Far joined us—a guide for Portland Bike Tours and native Portlander who knows more than anyone I know about local Portland history. He told us stories of the Portland Royalty—as he called them—the early founders of the city and the railroad barons of old.


The Montavilla neighborhood was rad and totally unexpected. It seemed so far from everything and although I knew there was one “hip” brunch restaurant there (the Country Cat Café), I had no idea there were awesome things all around it, too.

From there, we continued past I-205 into east eastern Portland towards Stark Park where the Stark Island Fountain is the most eastern Portland public art fountain listed on the Portland Fountain tour. Unfortunately, it wasn’t operating, but we were able to catch some tacos at a food truck parking lot on the way there.



So Far climbing up to the castle on Rocky Butte




Rocky Butte loomed to the north of us—an island of forest and trees and a clear landmark to navigate to. My research on topo maps had showed there are trails to the top not listed on googlemaps (as is the case in Forest Park as well). We had to do some exploration to find them, but found a way through the dense, moist forest up to the tower on top.

Despite the weather, Rocky Butte reminded me of Mulholland Drive in LA—it was a narrow road surrounded by giant, beautiful houses (but not nearly as tightly on the ridge as its LA counterparts).

SoFar assured us that the top of the mountain was awesome, and we continued up the road. He was right. There was a giant castle on the top constructed of lava rock. In the Portland mist, it looked like a Scottish castle with a view out over the Columbia river and Portland empire.


A giant tree at the Grotto


From Rocky Butte, my maps showed there is a trail down to the Sandy Blvd but there were no Trespassing signs, so we walked around the neighborhood. But, as is with urban hiking, it’s the adventures and the unexpected that make the trip. We found an unmapped mural intersection! It felt like stumbling across an Easter egg.

With wet hugs, So Far left us–missing one of the highlights of the day, the Grotto. We continued into the forested compound without him. Immediately, the energy in the air felt different than Sandy Blvd. There were giant trees and it was peaceful and quiet. It was a strange thing to find some beauty and solitude right on Sandy Blvd. It was unlike anything I’d seen in Portland so far and words fail me to describe the experience.


With a population of little more than 800, Maywood Park is a city within Portland

Much like Denver, Portland has a small city within its city limits. Here, it’s the beautiful separately incorporated city of Maywood Park. We walked its few blocks before heading on the long and less glamorous walk down Sandy Blvd and up to Marine Drive.

Marine Drive follows the Columbia River—which I had hoped would give us good open views up north and out to the east. Unfortunately, the weather didn’t provide, but it was still nice to walk along the northernmost boundary of the city.


A turtle loving home in the Cully neighborhood

SoFar told us he commutes everyday on the 205 Bikepath, which we took up to Sandy Blvd before crossing into the Cully neighborhood. Cully is a neighborhood with cute houses, big trees, and big lots great for urban farmers. It’s clear there are artists here and young families and the vibe here felt homey and good.

While north and north Portland may not be the glamour spots exhibited on Portland tourism ads, it was cool to see a part of the city that felt lived in and off the beaten path and to realize that there are so many bike and trail options even in the less forested areas. Today was a day of adventure and discovery and I feel honored to have shared it with SoFar and Virgo.