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  • Tim Mathis

A Template for DIY Pilgrimage and Backyard Adventure: Lessons from an Urban Thru-Hike in Portland

Updated: May 28, 2023

Maybe you want to go on a trip that will change your life.

The GAP Month is a framework designed to help you do just that. It’s a type of trip that’s meant to be both life-changing and accessible. You can read a lot more at the link but in short, it’s a month long trip that has the classic elements that make pilgrimage impactful. It involves significant time away from home (a month, give or take), human-powered travel, an element of adventure, personal rituals and intentions, and involvement from people you love.

One of the key problems for someone who wants to take this sort of trip is where they should go and how.

The easiest way to solve that problems is to just pick an existing route and go. There are plenty of long-distance trails, bike tours, traditional pilgrimage routes, and paddling corridors. You could just pick one and do it. It’s straightforward. That’s why hundreds of thousands of people do the Camino every year, for instance.

But what if you want to be more creative? What if you can’t go far from home? What if you’re the type of person enchanted by the idea of walking out your front door and off into the world, like in The Unlikely Pilgrimage of Harold Fry?

In that case, you can design your own route. You can make up the rules for your own life-changing journey.

Why would you want to do that? Maybe you don’t have the time or money to jet off to some remote locale. Maybe you want to follow the traditional pilgrim spirit and step out your front door and onto the road. Maybe you want to go to a place that doesn’t have an established long trail or pilgrimage route. Maybe you’re just the creative type and like the idea of choosing your own adventure.

In any case, this article is meant to help with that.

Staircase from Portland urban thru hike

How do you design your own epic adventure?

Early on as I was releasing these GAP articles, a couple of different people said that they’d like to hear some advice about designing their own pilgrimage routes close to home. I wanted to provide some guidance, but I wasn’t sure how to ground it in reality, not actually having done such a thing myself. While this article on Taiwan Cycle Route 1 covers some useful ground, it’s not really the same thing.

Then, I remembered my old friend Six2. While he maybe wouldn’t label what he does as “pilgrimage” per se, he’s organized this sort of trip multiple times.

So, I called him up and I picked his brain for nitty gritty details - from tips on planning to safety to transportation to budget.

And now, here we are: grounded in reality.

First things first, who is our adventure expert?

Six2’s name is actually David, but we met on the Pacific Crest Trail so I know him by his trail name. He got it on the Appalachian Trail where other hikers kept asking him how tall he was.

“I”m 6’2.”

After a few times the name stuck.

Six2 is one of those people who lives an extremely interesting life but doesn’t go around blogging about it. His adventures are personally motivated and he doesn’t normally self-promote. He’s a prototypical case study for The Dirtbag’s Guide to Life and I must have mentioned him in there at some point.

I met Six2 on the PCT, but a few years ago I also joined him at the end of one of his more madcap adventures, when we walked 30 miles on the WIldwood Trail which passes through Portland, Oregon. It was the conclusion of a months-long project that he designed himself - a more than 300 mile route that connected all of Portland’s public stairways (with more than 10 steps) into a giant, winding circuit through the city’s streets. I just did the last section. He completed the entire route.

This trip, I realized, was exactly what we’re talking about here. It was an eccentric, self-organized, human-powered trip in a non-traditional location that took on all of the elements of pilgrimage.

In short, it was a great trip to use as an example for an article about how you can design your own local pilgrimage or adventure route.

A few days before I wrote this article, Six2 and I spent an hour and a half on the phone talking about this trip. He’s nerdy enough that he plans meticulously and keeps the receipts, so he’s an ideal guide for this sort of thing.

These are the things we talked about that you should know.

(I’ll be “quoting” Six2 a lot the rest of the way - I should give the disclaimer that almost every quote is actually a paraphrase. It’s all roughly accurate though. None of it is wholly made up.)

A Portland stair pilgrimage, for example.

Let’s start by answering the question a little bit more concretely, what did Six2 do in Portland? It’ll give you some good ideas, I’m sure of it.

Six2 was keen for a local adventure, so one year he spent a bunch of time marking out all of Portland’s public staircases on a map, and tracing a route that connected them. Then, he spent his winter walking the circuit in sections. He didn’t take time off to complete it so he fit it in around work and domestic commitments (although he was only working part-time so he did have some degree of time flexibility). He didn’t go out every day but he did prioritize walking most days of the week, rain or shine. It took him a few months, and the trip concluded when he and I walked the Wildwood.

During the hike, he slept at home each night and primarily used buses to get to and from his route. He’d normally bus to the start and then back home from where he finished, connecting segments piece by piece. Some days he would park near a bus stop, catch the bus to a point miles away, and walk back to his car. Some days friends or his partner would help him out, dropping him off or picking him up. In the end, he’d walked the entire route.

Because it was winter in the Pacific Northwest, he often walked in the rain and occasionally snow, and because of his schedule he often found himself walking after dark.

This might seem like a strange thing to do, but he described a variety of motivations when I asked him about it.

He did it because, after years of summer excursions, he wanted a project that would allow him to spend long periods of time outside to help battle the doldrums during the PNW winter. He couldn’t easily get away from home, and wanted to get to know Portland better anyway. He loves planning and he “wanted to do normal things in abnormal ways.” So, taking inspiration from Liz “Snorkel” Thomas’s Urban Thru Hikes, he designed a route and completed it.

Planning the route

The fundamental problem for the DIY pilgrim is where to go - determining both your destination and how you’ll get there.

Six2 pointed out that, to some degree, you just have to make a call.

“Decision paralysis is a real problem. The possibilities are endless, but at the end of the day you just have to find something that interests you and go with it.”

For him, it was public staircases in Portland. That’s idiosyncratic and arbitrary, but it gave the trip a structure and allowed him to begin the process of building his route.

“[F]or me "every public outdoor staircase (with 10 or more steps) in Portland" added points of interest, I went to the top of big hills in town, checked out parks I hadn't seen, crossed all the big bridges with foot paths.”

The question for the DIY route designer is about what interests you. “It helps to have a theme.”

In order to spur ideas, SIx2 suggests following interesting people on social media (“You have to check out Beau Miles! I can’t believe I haven’t talked to you about him!”), and reading up on destinations that seem appealing. Then, make a decision on what you’ll do based on personal goals and interests. You could design a route between restaurants, historical structures, churches, or parks (The aforementioned Snorkel did this in NYC). You could walk between friends’ houses. You could walk around something big (Puget Sound or the San Francisco Bay), or you could simply focus on walking towards a destination that matters to you. I mentioned The Unlikely Pilgrimage of Harold Fry. It’s a fictional story, but also a charming inspiration for this sort of thing. Harold decides on a whim to walk out his front door and across England to get to an old friend who has received a terminal diagnosis.

Your destination, and the stops along the way, give structure to the experience but there’s not a magic formula. Ultimately, you pick some poles that interest you, and you move between them.

The traditional types of pilgrimage structures are either point to point or along a set circuit. You could also design a route that looks like a starburst with a series of out and back trips from a central point (like your house), or something meandering - a wander in the wilderness.

Some of you are planners like Six2 and may want to meticulously mark out your route street by street. He said that, for him, this was a big part of the fun.

“I realized that I just like planning. It was an excuse to learn about the city, and places that I never would’ve gone otherwise. It let me spend a bunch of time staring at maps and figuring out these secret, weird little pathways that no one uses anymore.”

For others, you might not care to determine more than your start and end points, and simply decide day to day how to move between them.

Six2 said that it’s important to consider what you want to accomplish both personally and physically with this sort of thing. What do you want to get out of this experience? Are you trying to get fit? Do you want to walk around your city, or explore a destination a long way away? Do you want to be in wilderness or town? What’s your budget in terms of time and money? Can you get time off work or do you want to figure out how to work within the bounds of your day to day responsibilities?

Six2 also said that it’s important to think about how you’ll know when you’re finished. You may pick your start and end points physically, but figure out in the middle that the experience is no longer serving your personal goals. So, you may decide to quit early. He said that he follows something that I’d call the “never quit on an uphill” principle. If you’re tired, and you want to quit, don’t let yourself do it straightaway.

“I have an old rule that if I want to quit, I mentally commit to continuing for three more days. If I still want to quit after that, then I can. I think it’s helped me build up resilience over the years.”

The goal is to make sure that you don’t end up giving up in a way that will mean missing out on what you were trying to accomplish personally.

Some waypoints on a Portland urban thru-hike

Tools for route planning

Six2 talked about a set of useful tools that he uses during the planning process for these sorts of trips.

First off, just go to the library: “I got out a bunch of books, those “Walking Guide to Portland” type books, and “50 hikes within 50 miles of…” I also found this old coffee table book called “The Stairs of Portland” that had pictures of the places I wanted to go.” At some point someone has probably written a book that’s related to what you want to do, no matter how weird it is.

Also, do some research online to see if someone has done something similar to what you’re planning in the past. There’s very little that’s new under the sun.

“There’s the Inman 300, for example, in L.A. where someone made a route between all of the stairways there.” Even if it isn’t exactly what you’re planning, finding other similar examples can be a great way to get inspired.

More concretely, “Transit maps are your friend.” He suggested that if you’re building a tour of a city especially, consider transit hub locations during your planning. You may need to access transit for a variety of reasons, and it’s helpful to work them in along the route.

The time-honored way to build a route is by marking it out on a paper map, but these sometimes don’t have the level of detail that you need, and tend to be car focused.

Generally speaking, maps and tools designed for cycling can be more helpful and available. (Local walking maps help, of course, but they tend to cover smaller areas because people don’t usually walk hundreds of miles at a time.)

Six2 suggested using in planning because it has regularly updated, ground level information crowd sourced from people actually using these routes. It’s isn’t a great site to use on your phone, but it is on your laptop.

The app Locus Maps allows you to access data from OpenCycleMaps on your phone.

The simplest, most universal tool for building a map online is MyMaps on Google Maps where you can build a route by adding pins at checkpoints along the way between your start and finish.

Personally, I’ve also used Maps.Me - It’s an easy to use tool for following downloaded GPX files on your phone, and when you have data you can use their walking and biking functions to identify routes on the fly that will be amenable to walkers or cyclists.

For non-urban areas, Six2 suggests, which allows you to build maps that it can break down into segments by distance.

Google Street View is also great because it allows you to actually look at where you’re planning to go, and figure out if it’s going to be safe or feasible.”

Safety during urban adventures

Planning an extended trip like this, naturally you’re going to be concerned about safety issues. There’s some level of risk involved with any adventure, but there are things you can do to go as safely as possible when you’re planning your trip.

For Six2, “#1 in safety for me, if it's an urban hike, that risk is probably from cars. I mitigate that risk by choosing routes that separate you from traffic. At one point in my PDX walk, I had to walk by traffic at night, not ideal. Good planning helps avoid that; Google street view, driving out to assess the route in advance, asking people who have gone that way before (forums, Reddit, Facebook). Most cities are safer than most people think, especially during the day when other people are out, but if you're not sure, ask local people about the areas you want to go, and get a couple opinions if it sounds sketchy.”

The challenge when designing a route is going where you want while avoiding sketchiness as much as possible. Not all areas are amenable to human powered travel. Having at least some cursory knowledge of where you’ll be passing through can help you avoid some of the biggest risks.


Because he slept at home every night, Six2’s gear could be pretty basic. He recommended wearing road shoes vs trail runners if you’re going to be on pavement a lot. He mentioned good rain and cold weather gear, a day pack, and a headlamp. Beyond that, for a trip like this, you just need basics like food and water for the day, a first aid kit, your wallet, your phone and a bus pass.

“The good news for urban hikes: people live in cities so basically whatever you might unexpectedly need you can probably buy.”

If you’re wilderness hiking or bike touring the lists will be different, of course. A good thing about something like Six2’s local approach is that it keeps gear costs down. That might be less of a concern if you already have the stuff.


An advantage of designing a route close to home is that you can conceivably avoid paying for accommodation by just returning to your house every night.

Barring that, the options include utilizing free housing networks like Warm Showers and Couchsurfing, designing a route that takes you near friends’ houses, or using paid options like hotels, hostels, and campgrounds.

Bandit camping is also a time-honored tradition among bike-tourists and long distance walkers.

I’m no pro, but this guy Tom is. This is a great guide to wild camping anywhere.

As you’re planning, you can design your route to arrive at set accommodation every night, or you can plan to just finds places en route. Another option is to move between transit hubs and use buses to get to accommodation if there are none near your route. Or, export Six2’s strategy and stay in one central location and use transit or taxis to get to your daily start and end points.


“My costs were really only transportation and food. It was $5 for a day pass on the bus. Food can be a problem because there’s always the option of stopping in a cool little spot.”

But maybe that’s the point? Maybe you want to try out the local food as a part of the experience.

“Some people want to stop at all the bodegas and cafes and stuff. If you want though, you can keep your food costs really low by packing your meals.”

The good thing is that - compared to other travel options - this sort of trip can be very low cost, particularly if you design a local route, stay with friends or figure out how to avoid accommodation costs with free options like Couchsurfing and wild camping. What’s cheaper than walking or riding a bike?

Gear costs, of course, will vary depending both on the type of trip you plan and the amount of gear you already own.


Six2 mainly used public transit to get to and from his route from home. He also drove to transit hubs at times, took the bus a few miles away, and then walked back to his car. Sometimes he got dropped off and picked up on route by friends or his partner, which helped. Taxis and Ubers are also an option in populated areas, but those costs add up quickly.

As you’re thinking about where you’ll go, consider looking for places with good local transit options, or plan how you’ll get by without it. (Cycle tourists know that a bike, of course, is a great life hack for this problem.)

Making sure it is pilgrimage

In my experience, if you do something like this, it’s going to take on meaning. Take a month off and it’ll change your life. I’m sure of it. The GAP formula works.

But Six2 spoke to some of the specific ways in which this was true.

“This walk was really how Portland started to feel like home. I hadn’t lived there for that long at the time. Through the hike I became a part of it and it became part of me.”

He also said that he had some poignant moments along the way.

“One night midway through, I was coming down this hill in the rain, it was dark and I was drenched and miserable and dirty. I came upon this little cafe and stood outside the window looking in. I just thought about the situation, like I’m secretly doing this thru-hike while everyone is just living their life around me. It felt weirdly subversive and revolutionary. I felt this sense of connection with itinerant pilgrims through history even though I was in my own city, not even that far from my house. I was having these experiences that normally you can avoid in the city - spending the day in the rain, feeling dirty and hungry. It was a moment!”

Scene from Portland Thru-hike. A cafe, outside looking in.

Six2 used the trip to connect to his local area, but he said that he also very much wanted a physical experience. “There is something essential for me about the challenge part, about the physical exertion. It's way different from a short vacation just to relax.”

It was a helpful process for battling Seasonal Affective Disorder, getting outside on short PNW winter days, and “with all of the stairs, I really got fit. It ended up being my biggest hiking year in terms of miles, and because I did that over the winter I was a lot more fit in the summer when the normal hiking season arrived.”

Bringing friends and family into the experience

You would assume that working people in to the experience would be easy if it’s in your backyard.

However, Six2 said, “I found that because I was going places that people had already been, I had a hard time convincing them to come out and walk all day with me, especially in the rain.”

“I did drag my partner along one day but it ended up being one of the most muddy and miserable days of the whole trip so it wasn’t really a good experience for her.”

He also said that he’d planned to share the trip online,

“But usually by the time I got home and cleaned up and walked the dog I didn’t feel like getting online. I talked with people about it, and I shared some photos, but it was less of a public thing than I originally thought it would be. It mostly just ended up being a thing I did.”

He did endorse chronicling these sorts of experiences carefully though.

“I’m not someone who obsesses over archiving. Some people do though, and for them it can be a really important part of the process. It lets them go back and relive it in a way they couldn’t otherwise.”

"The chronicling part is good for the purpose of inspiring others, and sharing with people who can't/won't do something like that."

"I prioritize the movement outside part over the chronicling - which is a personal choice! For some people, the chronicling might be the main activity."

We talked about the difference in community involvement in local trips and the ones he’d done in other areas. “I think the Couchsurfing thing is great. It’s a great way to meet local people and get local information.”

It also taps into the pilgrimage tradition of relying on hospitality of strangers. “You don’t even have to stay with them though. Sometimes I’ve just used it to organize a meetup for a coffee or something to meet people and get information about a local area.”

Pros and cons of an urban or local thru-hike

When we were wrapping up our conversation, I asked about some of the pros and cons of doing this sort of local walk.

“Keeping my carbon footprint down was a big one. Also I could do it without feeling like I was leaving my partner behind with all of the domestic duties. I could still walk the dog and make dinner. I passed through places where I never would have otherwise, and I saw things at a walking pace that people normally just drive by. It gives you some of the joy of thru-hiking but in the city.”

“It was also something I could do in the offseason when you can’t really get into the mountains safely. It wasn’t a wilderness experience but it’s surprising how much you still feel like you’re outside, even in the city.”

“I had one of my sketchiest river crossings ever on this trip, right in Portland. An old bridge had gone down and I ended up crossing a decent-sized river on a skinny, slippery log. It was terrifying. Then, on my way back I did find a bridge over the river, but I was meant to be going up this set of stairs that I found out had fully rotted away years ago. Someone had tied a rope in its place but I had to scramble up the side of this steep hill in the rain on loose soil and rotten wood. I was in the middle of the suburbs but I never got that dirty on the PCT!”

Sketchy log crossing on Portland Thru-hike

Still, “Logistics are easier because you have shops and buses and taxis. It’s probably easier for the average person to organize this kind of thing than a trip in the wilderness.”

Surprisingly “My feet actually had a hard time on this trip. Hard surfaces require different shoes. I switched to road running shoes because I’ve hurt myself in the past on pavement in trail runners like I usually wear hiking.”

In Conclusion…

The GAP structure is about taking the time and space to do something challenging and unusual, recognizing that it’ll have a significant impact on your life.

Talking with Six2 reinforced that it works in real life. From start to finish he talked about the impacts and exciting bits of his experience. For him, the planning process allowed him to nerd out, learn about his area, and imagine a big, personal adventure. During the walk he had experiences that he never would have had otherwise. He dealt with some real challenges and had some poignant moments. He got fit, and he looks back on it as a moment when he really bonded with his new home.

His experience also reinforced that a trip with the potential to be life-changing doesn’t have to be organized around anything magical or unique. Six2’s route was just about staircases. His destinations weren’t spiritually significant. They were just something to give structure to his planning and add points of interest along the way. You can design a pilgrimage route to pass through emotionally evocative landmarks, but even if your destination is mundane, it’ll work.

His trip also highlighted that meaningful travel doesn’t have to happen a long way from home. It’s the most traditional model of pilgrimage, actually, to head out your front door and walk along a circuit or towards a specific destination that you can reach on foot. The experience isn’t always about going somewhere distant. It’s about figuring out how to get to your goal safely, relying on the hospitality of strangers and your own ingenuity. This sort of local trip ticks all of those boxes.

Hopefully you’ve picked up some good ideas and resources in this article. Get in contact if you’re keen to discuss your own ideas. I’m always happy to talk with like-minded weirdos. Check out the other articles in the GAP Month series for more ideas and inspiration.

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