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Portland Urban Hike Day 9: Hidden Trails in the West



Last night, we stayed with my friend Heather, whose positive attitude turned around our day. We had dinner on what she called “Trendy-third street” (NW 23rd) where I actually chose not to get Salt & Straw Ice cream because the line was curled around the door—even at 9 pm in the rain on a Wednesday.

To make up for lost miles yesterday, we started earlier and hit the Washington Park stairs and those in the neighborhood. Our plans were stymied when a trail that led down to the Japanese Gardens was closed for construction related to the gardens, so we had to take surface streets there.

The sun was perfect and Virgo was having a field day filming in the park. We started on the official map for Day 9 around 9:30—the same time we’ve been generally starting each day after I finish my morning work.

From here, we hit up the classic Northwest Hills stairs. This are big stairs in beautiful neighborhoods. They are the kind of public stairs I love and am familiar with from other cities—take a big hill, put a grid on it, have every road deadend with a public stairway up to the top of the ridge.


After breakfast, we met up with our friend Carrie, who lives in the area and would run the stairs for training during her lunch break. It was fun using the map to show her a few new stairs—including on the strangely named Circus (yes, Circus is used as the directive instead of ‘Street’ or “Rd” or “Way” or “Ave”)

Despite the previously bluebird sky, it rained and rained hard for a good ten minutes as we entered Forest Park on the muddy and super steep Holman Trail. It was SUCH a respite to be in the peaceful park and just put one foot in front of the other.

That was—until it spit us out at the curvy, high speed, no shoulder 53rd Ave. We walked down to the even scarier Cornell Road near the Bird Sanctuary until veering off at the Collins Trailhead.

This was one of those days where everything works out. According to Google Maps, there are no trails that connect the Bird Sanctuary down to Skyline Drive except the Wildwood (which I am saving for Saturday and goes way out of the way). It looks like there is private property south of the Bird Sanctuary. But some sleuthing, looking and topo maps, and hiking forum searches turned up a little visited trail owed by the Bird Sanctuary that connects them all—the Collins Trail.

I wasn’t sure if it’d work and the intersection we ended up veering off on was for an unmarked trail, but it ended up leading exactly to where we wanted. We were spit out in the neighborhood far south that we needed—except there was a big gate separating us from the neighborhood. It looked like we were urban cliffed out behind private property. We reinvestigated, and the gate is to prevent people from the neighborhood from driving to the a water pump area, not to prevent pedestrians from accessing from either side.

The Meriden Ridge neighborhood boasts the newest stairs in Portland—long, never ending stairs up practically up to the OPB radio tower near Skyline Blvd. The houses in this neighborhood were ridiculously large. But that’s one thing I love about urban hiking and the sometimes seemingly foolish persuit of stairs—it forces you into neighborhoods you would never go. Where the wealthy may be inclined to think of public roads and public sidewalks as amenities of their own enclave of the wealthy—to start thinking of the neighborhood as an exclusive not-gated community—there was still public resources used there. The road and sidewalks and stairs there are built with public funds for everyone’s use, so it’s important that pedestrians go there to visit.

The walk down Skyline Blvd to Burnside was scary and fittingly hugged a cemetery. It was a relief to veer off into a neighborhood and take 58th Ave all the way down to US 26. After a long lunch, we braced ourselves for the fate we had ahead: walking Scholls Ferry Road.

Scholls Ferry Road has no shoulder, no bike lane, and twists and turns as cars go quickly down hill. There are no connector alternates from US 26 south that would work otherwise. Googlemaps said it was the best bike route simply because it’s the only route in that area. The road made me so mad—that for millennia, people have been able to access all sorts of places with our feet and hands and only relatively recently in history have we built these places where feet and hands do us little good in the face of large machines.

We finally veered off into a neighborhood and it was like night and day. We actually made jokes about how we had been hit by cars and gone to the urban thru-hiking afterlife: the road was carless, wide, downhill, with lots of sun, and there were flowers everywhere. It was so beautiful—especially in contrast to Scholl’s Ferry Road—that it was hard to imagine that the two places were so close to one another.

The rest of the day was a fun series of hidden stairs, alleys, and pedestrians paths signed by the SW Trails Association. We frequently saw the numbered SW Trails signs again. An AT hiker, Prefontaine, came and joined us for the last pleasant bit to Multonomah Village. It was fun to see what these locals described as “old Portland” or “90s Portland”—fun art, colorful yards, a little hippie in a Pacific Northwest kind of way.

From Multonomah Village, Prefontaine drove us to Next Adventure where I gave a talk on urban hiking and about my hike so far. It was a fun crowd of mostly thru-hikers, but there were a few people who were thru-hiking aspirationals who told me afterwards how inspiring the talk was. We stayed up late talking trail and gear. Day 9 was a varied day—a day of extremes—but that’s always been what I love about thru-hiking, whether in the mountains or in the city.

Portland Urban Hike Day 8

Virgo holding up his broken sunglasses
Virgo holding up his broken sunglasses

Miles: 12.5 miles

Starting: Grant Park

Ending: Nob Hill

Neighborhoods Visited: Grant Park,  Irvington, Steel Bridge, Old Town, Chinatown, Downtown, PSU, Goose Hollow, Southwest Hills, Burnside Bridge, Morrison Bridge, Nob Hill

So…for the 1st time in 7 urban hikes, I’ve been accosted. Virgo, who is thru-hiking with me and filming the Portland hike (and hiked the Seattle urban hike with me and made this great video), and I were headed from NE Portland over to the Steel Bridge. Now, this is a very public area and it was a sunny day. We were walking in broad daylight and there were tourists and families about. It happened in a place where I felt very safe. We were pumped about the day and about crossing over to the west side.

We were headed down some stairs towards the pedestrian bridge entrance and Virgo, like usual, had found a beautiful angle for me to walk through and was setting it up to get the lighting right. A guy came walking up the stairs saying, “Don’t f-ing take a photo of me.” Virgo told him, “Sir, I am not running the camera right now and wasn’t taking a video of you. I am just metering the camera.” The guy then did a high kick towards the camera and stepped on Virgo’s foot and got into his face as if he was going to fight him. Virgo remained calm (though I could tell he was holding back) and reassured the man that he had not been filming him. The man then lunged at Virgo’s face and grabbed his Ray Bans off his head and threw them to the ground, shattering them. Meanwhile, I watched on, shocked and too scared to be of much help. I was really impressed by how cool and respectful Virgo was. The man proceeded to make overtly sexual comments towards me while insulting Virgo’s masculinity (he must have assumed we were a couple). It was really awful, but we played cool, respectful, and waited until he left to continue filming.

We were both in shock. I really want pedestrians and urban hikers to reclaim their city, but I guess this was bound to happen sometime. I just didn’t think it’d be in Portland.

Not 10 minutes later, we were on the west side of the Steel Bridge and needed to go up some stairs. There were three homeless people sitting on the stairs with their shopping cart-ful of belongings blocking the entrance. Virgo knows that I’m a purist about getting all the stairs on an urban hike—a “rule” I’ve imposed on myself even though no one is watching (and no one cares, either). Even so, I told Virgo, “let’s just skip this stairway.” I was too shaken from the earlier incident to have another confrontation.

I’m so lucky to be doing this hike with another person, and one as street savvy as Virgo. He kindly and respectfully asked them if it was ok with them if they would move. They were actually very, very kind. Yet, when we walked between them, it was clear they were using drugs at the time. One guy was bloody behind his ear and on his hands and arms. It looked like he had just gotten beaten up. It was really heartbreaking to see, and yet I was still scared. People who don’t have the ability to get proper sleep due to laws or fear of being attacked are going through sleep deprivation. Having done a sleep study, I get that. You can be angry, irritable, unpredictable. Virgo told me afterwards that he was concerned they may try to stab him with a needle for his camera. It seemed like there were so many people, desperate and needy and addicted to drugs, who eyed his camera.

The stairs along the Morrison Bridge proved to be frustrating and dangerous. My Portland Stairway book calls these stairs infuriating—requiring pedestrians to go up and down sets of stairs so that cars don’t have to stop. These suspended stairways were filled with trash and needles. There were so many needles and tops of needles everywhere today.

Despite our dampened mood, nonetheless, we made the best of our time today. We visited Hair of the Dog Brewery. We walked through PSU’s campus and the North Block Park.

A highlight was visiting the Portland Montbell store on 10th and Yamhill and seeing Tommy and Panorama. I got some more warm and lightweight clothing before heading out back into the rain.

We visited the famous foodcart island and grabbed grilled cheese sandwiches before doing a mandatory ice cream stop at Ruby Jewell and visiting by Powell’s bookstore. Then we crossed over to the NW quadrant for the first time. I had kind of expected to feel safer in the NW quadrant, but we walked along a sidewalk stair near the stadium instead of taking the stairs because a couple was what appeared to me as having sex on the tunnel-like stair we needed to be on. Virgo said it looked like they were doing drugs. Either way, since it was a sidewalk stair, we could still get where we needed to go by walking the other sidewalk right by it. Yes, I know, now my urban thru-hike is invalid 😉

The trees today were gorgeous and as we went uphill into NW 23rd Ave, it felt like we were walking into a completely different planet than we had experience today.

The stairclimbing community in LA always told me that the best way to prevent crime in public spaces is to have people out and about walking—families, petwalkers, tourists, commuters. I still believe that and ultimately, one guy who clearly was having a rough day, shouldn’t make us forget about all the wonderful experience an urban thru-hike can offer.

What surprises me the most about the event was that outsiders—people who don’t live in Portland—never thought this could happen in Portland while locals were not surprised. Portland definitely has an identity bolstered by the TV show Portandia and by the trendiness of Mississippi, Albina, Williams, Alberta, Clinton, NW 23rd Ave. Outsiders were willing to forgive Portland and refuse to believe this could happen in Portland (myself included). For seasoned world travelers, what happened to us is not terribly notable. It just has never happened to me, and that’s why I found it so upsetting. Urban hiking—I suppose like backcountry hiking—is a game of numbers. Eventually, something is bound to happen, even if you make smart decisions. I’m just glad that no one was hurt and the only property loss was a pair of sunglasses.

Yet ultimately, it is a city with all the good things and all the bad things. We just ran into an “urban grizzly,” and although we were bluff charged, we didn’t get mauled.


Revisiting Familiar Places. Portland Urban Hike Day 7: Hollywood, Laurelhurst, Downtown, Old Town, Chinatown, Pearl District, Eliot, Irvington

Cool Moon ice cream!
Cool Moon ice cream!

Start: Beaumont-Wilshire

End: Irvington

Neighborhoods Visited: Hollywood, Laurelhurst, Downtown, Old Town, Chinatown, Pearl District, Eliot, Irvington

Miles: 14.2 miles

The day started with friends, food, and fun. Allgood and his dog Karluk joined us at for donuts at Pip’s Original, a Portland hot mini-donut place that we had been told was a must-visit.

From there, we walked through the beautiful homes in the Hollywood area north of I-5 including the historic Hollywood theater. We also stopped by the Mountain Shop, an outdoor gear store where I will be speaking about urban hiking on Tuesday, March 29th.


One of the trippy aspects of this trip for me is revisiting places I’ve been to in Portland before but doing it on foot. A few weeks ago, I flew into Portland for the American Long Distance Hiking Association West Cascade Backpacking Clinic and took the Max from the airport to Hollywood station. Now, on foot, I crossed the overpass from that station into the Laurelhurst station. Late at night in the rain, Portland and the station and all its stairs looked so intimidating. In the light, it seemed like a harmless connection between neighborhoods splits by I-5.

Pip’s Original donuts were so delicious, I forgot to take a photo of the food
Pip’s Original donuts were so delicious, I forgot to take a photo of the food

We immediately dropped into Laurelhurst, an old, beautiful neighborhood of big houses and big trees. The Laurelhurst Park—a Frederick Law Olmstead designed area—is the cornerstone of the neighborhood (besides, perhaps, a weird golden statue in the smack middle of it). The sun was out and turtles were sunning themselves on logs in the middle of the grand pond. A sign warning that stairs in the park can be icy seemed laughable. Sunlight hit the big trees and green grass and it felt peaceful and springy.

The icy steps of Laurelhurst Park
The icy steps of Laurelhurst Park

In the Laurelhurst neighborhood, we walked past the Laurelhurst Theater, where our friend Tomato (we stayed with him last night) works and is the world premiere theater of thru-hiking movies by Squatch Films and TBW Films. Basecamp Brewery, an outdoor themed establishment among thru-hikers managed by our friend Siddhartha (who we stayed with on night 1). The area around Basecamp has a soup kitchen and camps and is a sharp contrast to the clean, woodsy feeling of inside Basecamp. We stopped in to say hi before heading over to another neighborhood staple: Next Adventure gear store, work and funplace of my friends Dandy and Miss Info (who I stayed with on Day 5).

Little Free Library in Laurelhurst
Little Free Library in Laurelhurst

When I thru-hiked the PCT in 2009, Miss Info and I got off trail together and went into Next Adventure to gear up for Washington. The outfitter has been an employer of pre-trail and post-trail hikers for almost a decade. I’ll be speaking at Next on Thursday, March 24th (that’ tomorrow!) at 7 pm about my urban hike. Hope you can make it!

Sweet chicken yurt
Sweet chicken yurt

From Next, we headed towards some confusing stairs until the Hawthorne bridge. I don’t know what the neighborhood under the Hawthorne bridge is called, but I loved it. It felt like a port town. There was stuff from everywhere and it was dark and a little dirty and hard to understand on googlemaps. Before crossing the bridge, we dropped by the immaculate wooden coffee/lifestyle shop Coava. Re-purposed in an old industrial building, it felt even more LA or Denver than Portland. I love that airy, bright, former industrial feel, though, and felt more than anywhere, if I lived in Portland, I would go there to work from my laptop to feel hip and metropolitan.

Virgo at Basecamp Brewing with the amazing spicy kale salad from the food truck outside
Virgo at Basecamp Brewing with the amazing spicy kale salad from the food truck outside

I was worried about time crossing onto the west side. I knew there would be cool things to see! It seems like no matter how short a day of hiking is, it always feels rushed at the end because there’s so much to see, so much exploration. Just like an outdoor thru-hike, urban thru-hiking feels like it just hits the highlights of an area without deeply exploring. I only get to linger in the occasional restaurant. It’s never going to be as strong in immersing myself as the experience of living there for years. While urban hiking may be a more intense way to understand a city than normal tourism, it still pains me to walk past so many cool-looking places.

The locals call this one “four groins in a fountain”
The locals call this one “four groins in a fountain”

We went past the Pioneer Courthouse Sqaure and many Benson Bubblers and inoperable fountains. We visited the “Keep Portland Weird” mural and laughed at the obscene line at Voodoo Doughnuts. We passed from the pricey neighborhoods downtown into the greying Old Town/China Town and watched the transition into the Pearl District.

Urban wildlife fountains in Pioneer Courthouse Square
Urban wildlife fountains in Pioneer Courthouse Square

Towards the end of the day, I got my obligatory ice cream, this time at Cool Moon (which I had visited with my friend Aine about a year ago). This time, I had a decadent spicy chocolate cone that kept me toasty despite the rain that was falling on us. That trip with Aine reminded me how the Pearl ends abruptly to the north and how difficult it is to get over the railroad tracks and up to the Broadway Bridge. There’s so many new developments and construction there even compared to a year ago.

Dog drinking fountain in North Park Blocks
Dog drinking fountain in North Park Blocks

I’ve taken the train through Union Station many times—pretty much every time I hike in Washington, I take the train there and back. Yet, I haven’t ever walked through the neighborhood around it. On the underpass right across from the train station, we took some stairs down to see a man literally shooting up in broad daylight.

On a train layover a few years ago, I walked the cool bridge from Union Station over to this little neighborhood on the other side of the train tracks near the water. It’s hard to access, but nice. From there, we took stairs up to the Broadway Bridge and crossed among many a commuting cyclist. The current construction on the bridge made the non-motorized lane very narrow and I felt awful about my backpack taking up so much space.

Industrial Portland on the left is the last bit of the old Pearl District left
Industrial Portland on the left is the last bit of the old Pearl District left

From there, it was a pleasant walk to Irvington, where we enjoyed the restaurants. Once again, I found myself in a neighborhood I had eaten in before, but this time I knew here everything was and how it was connected. Besides Denver, Portland is the urban hiking city that I was the most familiar with before starting my hike. It’s strange how on foot, even a place that feels familiar can suddenly become exciting and new, while also feeling more connected.

Old Portland, New Portland: Gritty Industrial to Gentrified Urban Hiking

Northeast Portland has been the poster child for gentrification in a city that has been the poster child for gentrification nationwide. Today I hiked past the biggest examples of Portlandia today—the tiny house hotel, wooden high rises next to graffiti covered fences, and even the mural artist whose work is getting torn down with the building its on. It was a day of old and new Portland, as seen through the eyes of someone who doesn’t live here and as seen on foot.

The day started in Cully, a neighborhood which 20 years ago was considered dicey but now has blocks filled with Little Free Libraries (which I’ve been problematically obsessed with on this hike). It’s also become a neighborhood full of hikers—almost as soon as I left Miss Info’s home, I was as Toaster and Goodfoot’s house. What a small world!

Tomato met us at 42nd and Killingsworth and we headed through a beautiful park (and former school) towards 33rrd and Columbia—an area replete with a nasty series of curvey overpasses and underpasses with very small shoulders and fast moving cars. By car, these area looks impossible for an urban hiker, but there was a stairway to catch down from 33rd to Columbia Tomato, who lives in Portland as a car-free individual and walks in the city more than anyone I know, has experienced pedestrianism over 33rd and Columbia Lombard many times, but didn’t seem nearly as sketched as I was. I had looked at the area on Google Streetview and knew that a beautiful spiral stair existed in the area. Although no one was living under the overpass, we found a needle.

Walking Lombard was not fun. Tractor trailers splashed us as they zoomed onward. It was loud. Tomato told me a better route would have been to head north thorough the Columbia Slough area on nice trail and then meet up with 11th and Columbia (I had considered this route, but thought it would add at least 3 miles).

Finally, we made it to 11th and Lombard—just in time to see the train loaded with oil tankers coming by. Oil trains have become a political issue in the northwest because some locals are concerned about environmental or safety hazards of large quantities of oil moving so close to city center and neighborhoods. Train traffic is up 4 times, a big oil-by-rail terminal is in the works across the Columbia River in Washington, and as urban hikers, we walked through the heart of the controversy. Shortly after passing the train, we walked through a residential neighborhood with a No Oil Trains sign on the front lawn. This is what I love about urban hiking—understanding the local issues with national implications at a neighborhood-geographic level.

From there, we walked past several intersection murals to the incredible Penninula Park Rose Garden. Even this early in spring when the roses were not out yet, it was a stunning area. I went there to see a fountain (which I expected would be turned off) and was expecting a small, roadside few rows of roses—if I skipped it, that would have been all right. I did not expect a giant garden with a huge fountain that was running and a really cool looking pagoda. I can’t wait to return to the area when the flowers are in bloom!

Gentrification was just around the corner. We walked Albina, which my Portlandness book explained was the heart of redlining in Portland—at least until World War II when there was a huge influx of shipyard workers. Many African Americans at the time moved to Vanport, a shipyard workers city, until sudden 15 foot rise of the Columbia River flooded them out of home. Albina/Mississippi has become the example of gentrification in Portland. While I’d eaten hipster brunch here many times before, walking it forced me to read about its history and to see the history on its fences. Even the beautiful Rose Garden I had enjoyed so much a few blocks before had displaced African American families.

We grabbed tacos at Porque No? a famous Portland taco place that had a line out the door in the rain—even at 2 pm on a Monday. Virgo’s girlfriend Jamie and my friend Carrie joined us. After a leisurely lunch, we walked up Williams—another example of gentrification in the city. We got ice cream at What the Scoop?, famous for their fortune cookie waffle batter ice cream cones.


Lastly, we walked to Alberta, another neighborhood that has gone through a lot of change. There, we passed the tiny home hotel, the grilled cheese sandwich truck where you eat your meal in an old school bus, and a bunch of cute shops. A local mural artist chatted with us and told us that there were 271 different intersection murals in the city! Man, that is a lot less than the 20 or so I have mapped!

The day ended with Alameda Ridge—the old money swanky part of the northeast. We had fun in the Sabin Hydropark at the top of the hill and down through the many stairs of that beautiful neighborhood. Tomato walks the neighborhood a lot so he knew a bunch of the stairs, but it’s always super fun to walk with locals and discover something new.

Despite the weather, it was a fun and fascinating day in Portland and aside from the walk on Lombard, perhaps of all the days of the hike, the one I can see others replicating the most.




Portland Urban Hike: Northeast, Rocky Butte, Marine Drive

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
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
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
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
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.


Trip Report Urban Hike Day 4

This was the day I was looking forward to the most—an extremified version of the classic Portland urban hike, the 4 T Trail—a ~4 mile hike that takes travelers via trolley, train, trail, and tram in a loop through the west side of the city. In addition to adding miles, I added on the Tillikum Crossing—a pedestrian, bike, and bus/train only bridge! This day would exemplify the best of the non-motorized user experience in Portland allowing me to maximize the infrastructure.

I started in the Brooklyn neighborhood and hopped over Divis and through an industrial area and up stairs to MLK Blvd. This ended up “urban cliffing me out”—that is to say, that the stairs led up to a bus stop for users of the busy MLK, but otherwise wasn’t very walker friendly.

Luckily, Virgo knew the area well from his run route, so we went over the beautiful Tillikum bridge—a bridge for the people! Built in 2015, it was a joy to see so many families, dogwalkers, cyclists, runners, and tourists all enjoying Portland’s most beautiful central bridge (St. John’s being a beautiful bridge way north).

From there, we took T #2—the trolley—one stop to some stairways (the typical 4T route has users take the trolley all the way to the train). We grabbed some stairs downtown, passed a bunch of Benson Bubblers, and grabbed some of the fountains on the Portland Fountain Walking Tour. Sadly, they were not running, but some were just as beautiful. That would be one benefit of doing this hike a little later in the year—getting to see the fountains running. Nonetheless, as I tell people, March is the perfect time for me to do this hike because I’ll be in the mountains in the summer.

My buddy Sean met us at the Tom McCall Waterfront. We walked to Saturday Market together (the fountain there was working) and I used a Portland Loo, an idea that really shouldn’t be so revolutionary: having public restrooms available for free in places where people congregate for festivals, hanging with their friends, and being tourists. Portland has been hands down the easiest urban hike for me with regards to public restrooms. I can only hope that the rest of the trip will be as accident free.

After more stairs and bubblers in the city, Virgo and I trained up to the Oregon Zoo—a cool ride that goes under Forest Park through a tunnel. When you get off the train, you have to take an elevator up almost 700 feet! (I desperately looked for stairs and couldn’t find them). We crossed the busy thoroughfare

From there, the Marquam Trail was a respite from the busy city walking and we enjoyed some forest time before popping into a beautiful neighborhood high in the west hills with a killer view of Mt. Hood. There were long, secret, hidden stairs and windy roads here (which surprisingly had sidewalks—very uncommon for these mansion-filled hilly neighborhoods in my experience). There was even a Shell Station (=restrooms, water, food) on top of the hill, another anomaly for these kind of neighborhoods in my urban hiking experience.

From the Marquam Trail, we climbed to the OHSU campus and back down again via stairs including the Cliffhanger. Virgo’s girlfriend, Jamie, met us.

In addition to Kelly Butte (yesterday’s hike), one of the series of stairs I was most concerned about was the area around I-5 Naito near the Ross Island Bridge. It ended up being not as sketchy as I expected (both in terms of cars and people and confusingness).

We climbed back to OHSU with the tram looming above us. I was REALLY looking forward to the tram—I’ve wanted to take it for years and just have never found myself in that area everytime I come to Portland.

I told Jamie the experience of being at OHSU was like being in a sci-fi film. We were opening doors, going up stairs, walking through weird piped industrial halls looking for the way from the parking garage to the tram. It was like boarding the Death Star and looking and looking for a robot that we needed. The giant robot-looking like tram lured above us.

When we finally got to the tram, it angeringly closed at 5 pm and we got there at 5:10. We dissapointingly walked back down the hill. I went to where the tram would’ve dropped me off and Virgo caught a ride with Jamie back home. I had the fun experience of walking solo from that quickly crossing bottom-of-the-tram-OHSU-neighborhood-for-medical-people-with-money-for-food-trucks-and-condos over across the Ross Island Bridge, dubbed the sketchiest bridge for pedestrians. I longingly looked at the Tillikum Bridge where pedestrians don’t have to deal with the noise and cars.

From there, I was supposed to head to Ladd’s Addition by making a turn north, but couldn’t figure out how to get off Divis on foot (really, I couldn’t figure out how to walk north on Milwuakie). I ended up going south on Milwuakie all the way back to Brooklyn and then finally finding a pedestrian bridge over the railroad to take 20th up.

I was angry, upset, and hungry. It was getting dark and I was walking through the dispensary district which a friend had warned me wasn’t that great. When I finally got up 20th, though, it ended up paying off though—I found myself in the Clinton neighborhood and at Fifty Licks ice cream. This is sacrilege, but it was the best ice cream (not chunky, that is) I think I’ve ever had.

The rest of the walk was divine through Ladd’s Addition and then on Hawthorne back to Belmont. Just like a wilderness hike, urban hiking has its up and downs—it’s just on an urban hike, it’s a lot easier to find ice cream as an upper.

Portland Urban Hike Day 3

A cool thing about urban thru-hiking is how easy it is for your friends to join you along on a trip. This morning, my good friend Allgood and his four-legged friend Karluk met us in the morning as we walked through the beautiful iconic Mt. Tabor neighborhood.

Portland is the most volcanic city in the US according to my Portlandness book (which has a great map of the volcanic vents in the area). Mt. Tabor is a volcano sitting right in the middle of town. Virgo uses Mt. Tabor as his running route and showed us the way right past a volcanic lava tube and through stands of old pine and blooming cherry trees. From between all the vegetation, we were still able to get a straight view down Hawthorne and all the way to downtown.

A controversial and political dilemma in Portland right now is what to do with the reservoirs atop Mt Tabor. One hundred years ago, water was piped from Bull Run to Mt Tabor where it was stored as the public water source for Portland. After 9/11, the feds became increasingly concerned with water contamination and the area around the reservoir is under surveillance. The result was even in times of drought, hundreds of thousands of gallons of water had to be drained and disposed of after a man was found peeing into a reservoir. Now, as feds are requiring water to be stored underground, we saw one of the 3 reservoirs empty and it was ugly. Allgood, Virgo, and I had much fun speculating over what we would like to see happen with the 2 filled reservoirs.

We walked again towards 82nd where we had another obligatory stop for Asian food. I think it’s funny that several cities I’ve walked as a street called Division—which often does just that—divides town in a pedestrian unfriendly way. Virgo took me to a pedestrian overpass stairway on Division, which oddly enough was not listed in Laura Foster’s Portland Stairways book, the crowdsourced info I used from the Internet, or the Portland Bureau of Transportation list of public stairs. As I walk this route, I can’t help but feel the neglect that people on the other side of 82nd must feel from the world and local government.

Nowhere was local government neglect more noticeable on Kelly Butte.

Frankly said, I was concerned and a little scared about hiking up Kelly Butte. My plans, prep, and research showed that this Portland Public Park had essentially been neglected by the local government and allowed to be taken over by teenagers and the homeless. While all my interactions with the homeless in Portland had been harmless, and I’ve never had problems with people in LA, SF, Chicago, Denver, or Seattle, the secluded nature of Kelly Butte made it different than being out in the open on the street.

Sure enough, as we climbed to the gate that blocks cars, there was a homeless couple with a fire and graffiti everywhere. It’s funny, though, because the natural world up there was eerily peaceful and resembled the much more cared for Mt. Tabor. Kelly Butte is also volcanic—perhaps another vent from Mt. Hood—which is one of the reasons why I put it on the route. My apprehension about the hill wasn’t helped by Virgo joking that Kelly Butte is where people dump bodies.

While googlemaps showed the trail ending on the top, I looked at historic topo maps before I left to find where trails connected (satellite view for finding hidden trails is useless in Portland because of all of the tree cover). I found evidence of a historic trail headed off the southern side of Kelly Butte into the neighborhood. On an urban hike, almost every 100 feet and every turn is calculated and pre-determined. With Kelly Butte, my plan had been to “find a trail to get to the other side.”

As descended steeply off the butte, we found evidence of a homeless camp and all I could think was how to get off that hill. My heart racing to get off (meanwhile Virgo wanting me to go slower to get a cool shot), I jumped at the site of two people coming right towards us. Virgo and I have prepared mentally about what to do if we get jumped (he’ll eject his SD card to keep his footage before throwing his camera), and all those thoughts were racing through my head. Until I realized that the two people were kids going on a hike in their local park with branches as hiking poles. Phew! This—these local parks that kids can explore and play in and the freedom and trust to do it—is what I’ve been advocating for within cities. Seeing those kids playing on “scary” Kelly Butte warmed my heart and made me feel silly about the preconceived notion I had about the place based on what others had blogged.

After Kelly Butte, we walked through a series of neighborhoods connected by parks, the most notable being the forested Lent Park, which reminded me strongly of Columbia Park in NoPo where I’ve spent much time walking Karluk. From the Mt. Scott neighborhood, we walked the fun Woodstock neighborhood.

I stopped at Cloud City Ice Cream. Despite being overrun with kids, I was absolutely floored by their flavors. I love myself a chunky ice cream (Ben & Jerry’s is the classic example) and this place was chunktacular. I begged the scooper to let me try many flavors (while apologizing profusely and simultaneously asking how many flavors can fit into a 2 scoop). The winners: Better than Therapy (ginger chunk ice cream with ginger snaps), Animal Cookie (with whole size cookies inside), Chex Yourself (chex with caramel and chocolate), and hands down the best chocolate chip cookie dough ice cream I have ever had.

Ice cream in tow, we walked through the gorgeous campus at Reed College, which I found less intimidating than Lewis and Clark. We passed by some kids buildering (bouldering on a building) and chatted with them about the trip before taking a beautiful bridge over Reed Ravine to where the dorms are (does every fancy Portland college have to have a ravine running through it?).

The rest of the trip was through the more industrial area near Giant Brewing (where I had been particularly excited to visit after recently purchasing a bottle of their Ume Umami beer from a well-curated liquor store in Pasadena). The day ended in the Brooklyn neighborhood preparing for a big day heading out to the west side.


Portland Urban Hike: Day 2

Today seemed like the ultimate day of Portlandness—the expected, the unexpected, the tight community, the homelessness, the industrial, and nature.





Another highlight of the Southeast this morning was the Portland Pint Size Puppet Museum. It wasn’t open when we went by, but I can only hope to come by again later.

We headed out from Oak Bottoms over to the amazing painted intersection at SE Sherrett and 9th Ave. I had read about the painted intersections in the Portlandness book—but this blew my mind.


Each side of the 4 way stop had a piece of art, a handcrafted bench, a place for kids to place, or a free tea stand (!!!!). What??!!! This is the sort of tight community trusting love that Portland has a reputation for.

What’s funny is I mentioned that I visited this oasis to multiple locals, and they were almost jaded to the idea that such a magical place could exist. If only every town felt as trusting and supportive of their neighbors.

From there, we hit up a few nondescript stairs around McLoughlin before getting on the iconic Springwater Trail. It follows Springwater Creek and crosses over Johnson Creek—where Coho salmon have been found spawning recently in the city near some of the heavier industrial areas.


The trail then goes into an industrial area that smelled strongly of VOCs. Then we hit Cartlandia—a carnival of food carts. It was everything I hoped for and more and decision making was difficult to say the least.

We continued on the Springwater towards Powell Butte and were rewarded with a perfectly centered view of Mt. Hood.


The best thing I’ve seen in Portland so far was Powell Butte. I love this hike. As soon as we entered the woods, it smelled and felt like being in the wildlands. Both Virgo and I were immediately taken back to the PCT. The climb was gentle and the trail was well-marked. Like the absolute best well marked trail I’ve ever seen.

Powell Butte’s “peak” was like being on some of my favorite parts of the Appalachian Trail with Pacific Crest Trail views. It was like a grassy gently bald with views of three snow-covered volcanos. Dropping from that grassy bald back down into the temperate rainforest reminded me so much of being back in Tennessee on the AT that it was hard to leave because I loved it so much.

The rest of the day was immediately suburban sprawly—the sort that I didn’t really think existed in Portland. We walked on Holgate, a wide, fast-moving street. I was immediately reminded of where I grew up in Sacramento. It was miles and miles of Sacramento in Portland.

A highlight was stopping at the Chinatown east of 82nd. My Portlandness book showed that the immigrant population is moving from downtown to the very southeast part of Portland. After living in Denver, when I travel, anytime I see there is a Chinatown around, I get pretty excited to hunt down good Chinese food. Virgo tried chicken feet for the first time. He did not like it.

The day ended with a pleasant walk through southeast past murals, funky art, and cool digs. Today was a day where I saw the many sides of Portland, but it was all good.

Portland Urban Hike Day 1


Portland Hike: Day 1

Starting Point: The most southwest corner of Portland near PCC Sylvania

End point: Sellwood near Oak Bottoms

Mileage: 19.2 miles


Many locals don’t know how far south and west Portland City Limits actually goes. We started by Portland Community College Sylvania—quite near Tigard. Almost right off the bat, we got to travel on muddy trail through the forested Lesser City Park up to the campus—and then from there, do a little “cross country” hiking through a forest on the college’s property down to G Street.

To prep for the hike, I bought the infographic maptacular book Portlandness, a cartography geek’s dream created by two geography professors at PSU. The profs ran stats showing that Portland has way more unpaved streets than other Cascadia towns and I told Virgo, who is thru-hiking and filming the trip, “I really want to see some of these 4WD city streets!” Who would’ve thought that I’d find what I wanted so quickly into my hike?

The SW Trails Association has put together this great routes that serve like “bike routes” except for walkers. They take advantage of trails, stairs, and hidden alleys where only those on foot can go. I frequently found that although I hadn’t consulted with the SW Trails guide to map my trip, I was often on one of their routes.

I’m convinced not only is Portland the land where young people go to retire, but also where school age children go to retire. Despite walking on the fantastic stairway down to Jackson Middle School at 10:30 am, kids seemed to be going to coffee, hanging out, and doing anything but being in class. Maybe it’s spring break?

A fav spot of the day was the trail along Foley Balmer Natural Area along Tyron Creek. In a neighborhood that felt like walking through a tree house, close to a near-gated community, was a hidden trail system with beautiful rockwork. These are the gems that I seek on my Portland hike—that which is hidden from cars by leaves.

A crossing of I-5 and PCH/SW Barbur Blvd. brought us to a grittier area that Virgo told me was more like the “old Portland.” Already in this hike, I’ve heard a lot of folks compare new and old Portland. As an out of towner, I can’t make judgments because I have no past understanding to compare to what I see now. As a pedestrian, I want to understand and document to memory how Portland right now, and how its future is tied to its past.

One of the coolest things I’ve seen on any urban hike is the long unpaved alley climb up SW 19th Ave and the giant disc golf park up top. Then, we took a steep trail to Stephens Creek Natural Area just stunning. I can’t believe how lucky people in Portland are to have that be their neighborhood park.

Just south of I-5 in the Burlingame neighborhood, we found a cool series of stairs with the best yard art ever. Virgo and I probably spent near half an hour finding hidden toys in the trees before taking a hidden trail under the I-5 overpass. It’s funny that when you’re looking for beauty, even the highways appear beautiful.



The longest stairway of the day was SW Custer which spit us out Taylors Ferry Road—a dangerous, unsidewalked thoroughfare filled with commuters headed home. In an attempt to avoid the danger, we tried to reroute along what turned out to be an even sketchier SW Macadam Ave. Then we tried to hop on a railtrail along the Willamette—but it was closed due to construction. Ultimately, we backtracked and headed back to the pedestrian and biker unfriendly Taylors Ferry Road as it was the only path headed south.

Luckily, we were saved by the (strangely official) bike route through the River View Cemetery—a peaceful respite from the cars below.

One of the goals of this trip is to hit up all the colleges and university in Portland. Lewis and Clark College was among the more gorgeous campuses I’ve ever seen—and we enjoyed taking a break to use their gender neutral bathrooms.

Googlemaps made it look like we would have to go all the way south to Riverwood to connect Lewis and Clark bluff down to S Riverside Drive. But I had a sneaking suspicion that we’d be able to find a hidden trail down Lewis and Clark Ravine—and it worked!

We hopped on the rail trail along the Willamette all the way up to the Sellwood bridge—which just opened last week. Unfortunately, the pedestrian/bike lane on the northbound side wasn’t open yet so we had to sneak by a non-existent shoulder alongside commuters waiting at the bridge stoplight.

The day ended with gorgeous views of Mt. St. Helens and of the Mausoleum by Oak Bottoms. The end of day light was perfect to walk through this little nature reserve in the middle of the city.

Tomorrow brings a big chunk of the Springwater Trail and Powell Butte. Stay tuned!



Portland Urban Hike: Day 0

As I write this, I’m on a plane from Denver to Portland to begin a 210+ mile urban hike of the city of Portland. The Rose City has been my home away from home (and the trail) for the past few years and people have been telling me pretty much from the moment I started urban hiking that I need to walk it. Starting tomorrow, I will begin a 210+ mile traverse of the city over 13 days.

The City’s reverence for the pedestrian (and cyclist) is legendary. I haven’t even started the urban thru, and I am already blown away from the Portland Bureau of Transportation’s incredibly detailed and thorough walk/bike maps (seen in photos below). These maps are free, in full color, and PBOT even paid the shipping to mail them to me in Denver for my planning (and I ordered them online without even having to talk to anyone!). I highly recommend them to anyone who lives in the city, is visiting, or works as a city planner or pedestrian advocate. For the Portland hike, I’m expecting safe walking, respectful drivers, and lots of fun hidden pedestrian paths.

Distinct from my urban stairway walks elsewhere, the Portland trip is designed to highlight more than stairs. This trip will include:

  • 196 public stairways (plus a dozen more citizen-maintained stairways not on the list)
  • 9 bridges
  • 80 Benson Bubblers (Portland’s iconic street-corner drinking fountain)
  • All 5 quadrants (yes, although “quad” means 4, Portland has an extra)
  • Large portions of the Springwater Trail and Wildwood Trail (designated as a National Recreation Trail)
  • All of the volcanoes (Mt. Tabor and Rocky Butte, as well Powell Butte and Kelly Butte—Portland is the most volcanic city in North America)
  • All of Portland’s intersection murals
  • All the public Fountains on the Fountain tour
  • Most of the public art listed on the PDOT’s maps
  • Numerous heritage trees
  • Almost 2 dozen nights staying with supportive friends enthused in this walking experiment

And lastly…

  • Two talks about my experience walking Portland at two Portland iconic gear stores. I speak at Next Adventure on March 14th and at the Mountain Shop on March 29th.

Also unlike my other urban hikes, this Portland hike is designed to be replicate-able for someone of relatively physical fitness interested in walking or biking in the city. Mileages for each day range from 8-18 miles per day (much more reasonable than the 35’s I pulled in Los Angeles). The goal is that each day could be replicated by other hikers using public transit to access the start and finish.

Similar to the urban hike of Seattle, I hope to post daily logs of my journey and what I find. Miguel “Virgo” Aguilar will be hiking with me and filming the experience, so we hope to also have video to inspires others to explore the city.