I spent most of my first month in Portland parked in Buckman. It was a great vandwelling homestead—lots of shade, flat streets, tolerant (or clueless) neighbors—but when a nosey neighbor spooked me, I decided to leave the verdant Southeast and see what else my new home had to offer. 

While driving around the west side of Portland—a sloping urban maze of harsh contrast between the haves and the have-nots—I thought about the paradox of choice. Where is home when you can be homeless anywhere? I spent the next few days trying on the other quadrants of Portland for size. 

Southwest Portland: The proximity to downtown makes free overnight parking in this quadrant a major headache. The only residential area that looked ripe for vandwelling was Goose Hollow, an upscale neighborhood situated in the foothills of Washington Park filled with palatial estates painted in pastel colors that must have been aped from a travel magazine feature on Charleston. There was shade galore, but the flattest street I could find still had me sliding off my Thermarest pad several times throughout the night. The humor of sleeping in a $1,100 van in front of a $2.9 million dollar estate wore off long before my headache did the following morning. I skipped looking for a coffee shop and rolled my home back down the hill. 

Northwest Portland: In theory, the industrial end of Northwest Portland is a vandwellers dream come true. The area around NW 21st is populated with parking lots and warehouses that are empty after 5 pm, which equates to few neighbors and free parking galore. The Pearl District— home of 24 Hour Fitness, Safeway, and Whole Foods—is a short walk to the east. The coffee shops, bars, and restaurants of NW 21st and 23rd avenues are even closer. After a shower and a quick trip to the Safeway, I settled into a nice spot under a tree behind a generic-looking warehouse. The street was completely void of human life, save a couple box trucks and a dirty sleeping bag next to a dumpster. I slept peacefully, and woke up early the next morning to get some coffee. I strolled in the direction of 23rd, took a left, and was almost run over by a Porsche Boxster with a chihuahua in the passenger seat within three blocks. The air smelled like cheap cologne and desperation, and it was barely 9 am. I arced back to 21st and ended up at Coffee Time, where I was approached within 5 minutes by a shaky woman with curly blonde hair that looked like it had just been washed in the sink of the bathroom she emerged from. 

“Do people bother you all the time?” she asked with a sideways glance. 
“What?” I replied as I took my headphones off. 
“Well, you look a lot like Charles Manson...I figured people ask you about him a lot.” 
“Are you serious?” 
“Dude, chill out. It’s a compliment.” 
“He was a serial killer!” 
“Psh. He was....he was so much more than that....” 

The woman went back to her heap of torn Fred Meyer bags in the corner and mumbled something under her breath while looking at me. It was time to leave. I walked around the Pearl in search of a less weird place to get coffee. Each shop I happened upon was filled with pairs of middle-aged guys that looked like they used the term “power lunch” and had their iPhones clipped to the waist of their designer jeans. Women with giant sunglasses and boob jobs stumbled around in small herds, presumably drunk on wine and the feeling of valor that comes from knowing you’re above having to work for a living. This side of Portland was alien to me. It felt like the part of town where people end up when the career opportunity of a significant other involuntarily drags them kicking and screaming from their lofts in Manhattan and West Hollywood. 

I went back to the van for solitude, only to be disturbed every ten minutes by suburbanites in Volvos trolling for parking spots. The deserted street I parked on gradually transformed into a parking lot for yuppies that played tourist in their own city on the weekends, a few of which made comments about my van as I heard them traipsing by en route to Trendy Third. I assumed they would all be headed back this way in a few hours, loudly reminiscing about their college years in the street before they pilot their Land Rovers back up the hill. It was time to leave Northwest Portland. 

North Portland: By the time I turned on to Mississippi Avenue from Fremont, it was almost 8 pm. Traffic was gridlocked as drunk kids with flannel and greasy hair spilled into the street from bar after bar after bar on a Thursday night. After idling behind a Subaru that spent five minutes negotiating a parking spot big enough for a school bus, the van died in the middle of the street. As I turned the key and prayed my home didn’t clunk out for good, the apprehensive stares of inebriated passersby made me feel like the kid that peed his pants during naptime in kindergarten. The engine finally turned over and I made a quick left, eventually parking on a cramped side street a few blocks away. 

Beyond the road being flat, I no longer had the energy to care what my surroundings were. I went back to the main drag and found a solitary seat at the bar of a tragically hip German beer hall. I drank a pint alone and wondered if I would ever walk down this street with my own posse of rowdy friends, a group capable of turning a previously rundown neighborhood into a real estate prospectors wet dream. I went back to the van, put in a pair of earplugs to drown out the screams of the drunkards three blocks over, and went to sleep. 

Northeast: The sun hot-boxing my van woke me up bright and early on a Friday morning. Determined to find a greener place to call home, I took Fremont east and wound up in Irvington, a tony neighborhood filled with flat streets, giant trees, and stately mini-mansions that would have robots mowing their yards if it weren’t for Portland’s fondness for goats as an eco-friendly lawncare solution. Between the drifters loitering in front of the nearby Safeway and the army of vans parked on the side streets off NE Broadway, I pegged Irvington to be tolerant of vandwelling if it was kept tastefully under wraps. Moreover, a few houses even had old Westfalias lying dormant in the driveways, stowed away behind Audis and BMWs to serve as proud reminders of the owners' wilder youth before they got law degrees and became real adults. I parked around the corner from one, hopped on my bike, and rode to the 24 Hour Fitness in the nearby Hollywood neighborhood. I took a winding path home through the wooded avenues of wealth and good taste that make Irvington a classy alternative to the boredom of prefab suburbia, sleeping without a stir after going to bed before 11pm. 

The rattle of a neighbor’s lawn service crew woke me up bright and early the next morning. I decided the racket was unbearable, so I crawled into the driver’s seat and fired up the engine in hopes of moving to a quieter street. As I put the van in drive, I looked down and noticed I was shirtless and still in my boxer shorts. I looked to my left and saw a young mother with pearls and a sleeveless pink Ralph Lauren shirt staring at me from her porch with a look of befuddlement while her young daughter assembled a lemonade stand on the curb. I drove away in haste and paid little attention to where I was actually going. I eventually found myself near Northeast Davis and 28th Street, right around the corner from Beulahland, my beloved bar of choice during my days in nearby Buckman. 

Southeast: I spent the first half of the day idly drinking coffee in a funk. The other quadrants of Portland were certainly liveable, but they didn’t feel like home. The cart pod around the corner with the port-a-john that was never locked when I needed it most felt like home. Beulahland and its apathetic servers that let me spend hours doing nothing in the corner felt like home. I wanted to stay here, and to do that I needed to get my shit together and fly under the radar. 

Between rounds of Galaga, a coworker texted me an invite to a party. I rode past the shady spot in Buckman I abandoned a few days prior and wondered if it would ever be safe to go back there. I rode south past Hawthorne and Division, taking a short detour on the latter to see what I missed when I was content with staying on the same block up the street for three weeks. I made it to the party and mingled with some co-workers who were talking about their respective neighborhoods. I thought about the importance of being covert in my vandwelling, and wondered if it was a conversation that was best avoided. I considered the vast swath of culture in Southeast I had completely missed out on, and told my new friends that I was thinking about moving to this neck of the woods some time soon. 

“Good luck finding a place,” I heard someone say. 
“Yeah, rent down here is getting ridiculous.” 

As I walked back into the house to get a drink, I saw an empty spot on the street under the foliage of the massive oak tree growing from my friends yard. That spot has my name on it, I thought to myself. And it’s free.