The Alley Sweeper Motorcycle Rally In Portland, Oregon - 2019

An urban enduro surviving in a modern world.

Motorcyclists ride past homes and man in robe.
The occasional disgruntled homeowner was par for the course when it came to Alley Liberation, but “Robe Guy” was the day’s standout example.Jake McDonald

The world is changing—and fast. The rise of social media has placed us just a few clicks away from sharing any harebrained thought with the collective hive mind. This newfound power can be a honed, double-edged sword if you’re hoping to get your kicks in the murky gray areas of legality, ideally without falling under the ever-watchful eye of Johnny Law. Such was the ballad of the Alley Sweeper Urban Enduro.

Motorcycles lined up at FoPo Tavern.
It was a packed house at FoPo Tavern, the rally’s decade-old traditional starting point.Jake McDonald

This moto rally can be traced back to its 2009 inception by the hands of Portland, Oregon's Sang-Froid Riding Club, after club member Zac Christensen got the notion that an urban enduro through the city's less-affluent neighborhoods and sprawling network of derelict alleys might be a good idea. Where some might see a troubling disparity in public maintenance allocation between these areas and Portland's wealthier districts, Sang-Froid saw an opportunity for adventure in the long-forgotten back passages that fell through the cracks.

Man looking at Motorcycles for the Alley Sweeper.
The Alley Sweeper was fun for all ages, when it came to the bikes involved.Jake McDonald

And they weren’t the only ones. Word spread through all channels of social media like wildfire, as subsequent years saw the annual run’s attendance balloon to more than 400 riders. The alleys choked to a standstill as hordes of would-be scofflaws all dove in for a piece of the action, and it became clear a tactical correction needed to be made. So in 2015, the event was “officially” shut down. Clever. Its leadership became decentralized and eventually morphed into the clandestine Alley Liberation Front. The tide receded and the hysteria fell back into obscurity as only a handful of the most dedicated miscreants set to work planning future years quietly among themselves.

Fanny pack affixed to the front of a scooter.
Surely, nothing says “nothing to prove” like a fanny pack affixed to the front of a $100 scooter, emblazoned with the words “Nothing to prove.”Jake McDonald

Their strategy apparently worked, as the good word of the Alley Sweeper never came to me by any cliché Instagram post or wide-reaching Facebook promotion. Oh, no, my call to the Urban Enduro was conceived by a hushed whisper over a jar of moonshine, in the back of a short bus loaded to the gills with 200cc minibikes. You see, when Speedfreak Speed Shop gets together with the Gambler 500, we just can’t seem to help ourselves. “Let’s do the thing on minibikes,” Gambler Godfather Andy Munson cracked with a firewater grin. Some friend—surely the traffic courts already had a price on my head, yet he knew it wouldn’t take much more than the promise of senseless adventure to sucker me in.

So it was written, so it was done. A few weeks later I found myself on hallowed ground outside FoPo Tavern, the rally’s decade-old traditional starting point. Alongside me was a haphazardly assembled squad of guerilla fun-havers, our arguably illegal Coleman minibikes hastily camouflaged with homemade “49cc” decals and $13 bicycle safety flashers. Thrifty Southeast Asian riders would’ve stared in wonderment.

Bikes lined up in front of FoPo.
The front row lineup outside FoPo was packed with bikes upon arrival, and spilled out into the adjacent parking lot as participants kept rolling in.Jake McDonald

And, indeed, so did a few bystanders as I walked through the field of oil-burning dreams; a sea of dual-sport enduros of every make under the sun, easily matched by a population of either unplated or suspiciously plated dirt bikes. Not to be left out of the scramble, and true to "keep Portland weird" form, a subset of vintage bikes, mopeds, and a Ural sidecar also littered the scene. All told there were about a couple hundred participants. Eventually we made our way to the only real evidence of organization, a lone folding table with a stack of "course" maps, stickers, and event T-shirts. We were just in time, as the event unceremoniously kicked off and groups began sporadically blasting away down the street.

Further inspection of our map revealed less of a defined course, and more a vague suggestion of highlighted neighborhoods whose alleys needed liberating. Good enough for us; we ripped our pull-starts and unleashed our miniature machines on the nearest four-lane public thoroughfare.

Bikes at the Portland Alley Sweeper.
Our little Colemans were just weird enough to be at home among the field of oil-burning dreams.Jake McDonald

The previously gloomy sky now pierced with daggers of morning sunlight, we joined another cluster of bikes as they veered off down a nearby side street. Surprisingly, after all the talk of irritated homeowners coming out to protest the mob of hooligans invading their neighborhoods, we were instead greeted by families either lining the sidewalks or perched over their backyard fences, happily cheering us on as we launched into the first set of alleys.

Smiles widened and cheers broke out when I picked the front wheel up past a group of kids, and into a jungle of overgrown bushes, blackberry vines, and knee-high weeds. Instantly the draw of this urban enduro made itself clear as we ripped through the undergrowth, vines and branches clawing at us like antibodies fighting off foreign intruders.

LED flashlight electrical-taped over presumably dead OEM headlight.
My favorite part of this little Trail 90 was the LED flashlight electrical-taped over the presumably dead OEM headlight. Modern problems require modern solutions.Jake McDonald

Eventually the tangle would recede, and our little 200cc motors could sing up to their de-governed, 30-whatever-mph top speed as we hilariously picked our way through a flotsam of refuse. It was a symphony of chaos. Intoxicated with glory, we dodged random cinder blocks, grimy couches, and abandoned shopping carts through the lingering curtain of two-stroke haze. Truly, this was the most sublime form of anarchy.

Soon enough though, the neighborhood fun-police got wise to the incoming waves of two-wheeled delinquents and made their opposition known. We passed a disgruntled homeowner standing in the alley in nothing but his morning bathrobe, scrutinizing us with a look of simultaneous awe and irritation. There were warnings of a guy throwing steel chairs at riders a couple of blocks away. And when we stopped on an inconspicuous side street for some minor bike repairs, we were kindly confronted by a lady who made herself known as “the one who went on the news last year to speak out against all this.” Her biggest complaints were a few minutes of noise, and some mud being splattered across the pristine gravel surface of the public right-of-way behind her home. Insistent though she was, I wasn’t hearing anything worth ceasing my onslaught of alley recreation.

Motorcycle with rainbow circle under it.
One can only assume this thing has been sweating horsepower since the ’70s.Jake McDonald

So we carried on, as the day passed in a frenzy of adventure. We’d find ourselves lost in the labyrinth of overgrown passages, but it never took long to spot another band of roaming marauders to link up with. The rally, in truth, was a free-for-all perfected, and somehow all the chaos still led us to the aptly chosen finish line at the Alley Way Bar.

There awaited the final challenge for anyone all but completely lacking in self-preservation: a crudely constructed plywood jump that, to anyone on a suspensionless death machine, was more of a joke than any serious suggestion of flight without consequence. But ho! The siren song sings its promises of glory, and the call to Valhalla proved irresistible to our Speedfreak comrade and resident luck-pusher, Tyler Reitzer. Prior to that moment, I’d always wondered when we would meet an altitude that was beyond our skill level. Turns out, it’s somewhere around five and a half feet. The alley accepted its offering of broken man and machine, and glory was granted as Tyler sank into a handily presented wheelchair to the sound of onlookers’ thunderous applause. He thumbed his nose at death, and raised a final thumbs-up of defiance before being wheeled into the bar for a victory drink.

Illegal license plate on bike.
Upon inspecting this guy’s attempt at camouflaged legality, the longer you look, the less legal it gets.Jake McDonald

Even with his freshly scalped knees, our wounded friend was in agreement; it had been the perfect day. The smiles and thumbs-up had made up for the occasional chair-throwing protester, and the laughably senseless thrills easily compensated for any injuries sustained. This was the kind of fun that some would argue should be illegal. The kind that would’ve been quickly extinguished, had it continued above ground, a monster built of its own success and social-media hype. But thankfully the Alley Liberation Front had the foresight to know better, and take this last bastion of legally ambiguous depravity back under the radar. So, for now at least, it still lives there, safe from the outside world and ready to bestow foolish thrills upon any hooligan worth his weight in bad decisions—as long as you know where to look.

Squad of guerilla fun-havers on motorcycles.
This squad of guerilla fun-havers was just the latest example of what happens when Speedfreak Speed Shop gets together with the godfathers of the Gambler 500; bad ideas executed perfectly.Jake McDonald
Speedfreak Speed Shop’s custom Coleman CT200-U in front of wall.
My alley-sweeping weapon of choice was Speedfreak Speed Shop’s custom Coleman CT200-U, modified in a spoofy homage to Dakar legend Gaston Rahier.Jake McDonald
Motorcyclists in back passages of southeast Portland.
The derelict back passages of southeast Portland were returning to nature; half the time you weren’t sure the alley had ever even existed.Jake McDonald
Motorcyclist riding through foliage overgrowth.
At times, the scene of nature’s creeping stranglehold could readily be mistaken for something out of an Indiana Jones movie.Jake McDonald
Chuck “Buckshot” Brazer with bike and vine.
Chuck “Buckshot” Brazer emerged victorious from the jungle, but picked up some vegetation along the way.Jake McDonald
Biker riding through puddle in Portland.
The light, early morning showers only made things more hilarious, as we ripped across muddy potholes and blasted through standing water.Jake McDonald
Bikers riding down dirt trail.
Urban dirt biking had become our new favorite thing, and the line of bikes behind us said we weren’t alone in the sentiment.Jake McDonald