In a city of 6 mil­lion, one dis­carded eddy cre­ates great­ness—a trail at a time—re­veal­ing a rowdy rid­ing scene with stead­fast soul.

THE PARK­ING LOT AT TORONTO’S CROTHERS WOODS TRAILHEAD DOES NOT REVEAL ITS SE­CRET. If you be­lieve the kiosk, a few lit­tle trails spi­der down a hill and around some forested flats, form­ing a pleas­ant, if in­signif­i­cant, net­work of be­gin­ner-friendly sin­gle­track.

When we ar­rive, at 9:30 on a Thurs­day morn­ing in Oc­to­ber, only two oth­ers are there. A friend has ar­ranged for us to meet a lo­cal bike me­chanic for a tour, and an­other reg­u­lar has joined him. By tomorrow morn­ing, af­ter nearly eight hours of ped­al­ing, it will be clear that Toronto holds the most un­likely promised land in North Amer­i­can moun­tain bik­ing, a bounty of such chal­lenge and char­ac­ter and un­fath­omable va­ri­ety that I will strug­gle to ex­plain it for months. But now, stand­ing across a swath of as­phalt from the Loblaws gro­cery store, I can­not help but think the Don River Val­ley has been overblown by lo­cals who need to get out more.

An­drew Mae­mura, our 35-year-old tour guide, who goes by Maki, fid­gets off to the side as his child­hood friend Matt Mor­rish, photographer Bruno Long and I don shoes and packs. Paul Stu­art, 39, a con­struc­tion worker who has been rid­ing in Toronto for 27 years, rests on his dirt jumper, suck­ing on a cig­a­rette. A wal­let chain hangs from his jeans.

The trail net­work, in a pair of glacial ravines known sim­ply as ‘the Don,’ car­ries an al­most myth­i­cal rep­u­ta­tion among those who fre­quent it. With 60 miles of hand­built sin­gle­track wedged in a city of 6 mil­lion people, it’s hard to com­pre­hend how it re­mained a se­cret for so long. But be­fore Trail­forks and Strava, only those who knew some­one—or were will­ing to spend hun­dreds of hours ex­plor­ing—had any idea how ex­pan­sive

it was. “It was kind of like ‘Fight Club,’” one lo­cal told me. “Hon­estly, in the early days, you did not talk about trail en­trances and ex­its.”

We pedal down an of­fi­cial trail that soon gives way to an un­of­fi­cial rib­bon through the fo­liage, spit­ting us out at a home­made freestyle play­ground with dirt jumps and a pumptrack. Stu­art, known as Dig­ger to some, ba­si­cally lives on this dirt. He emp­ties the trash cans, pushes a wheel­bar­row, shov­els clay and mans the grill. Some­one once did 201 laps on the pumptrack without ped­al­ing, he says. “I counted.”

Maki waits on the edge while Dig­ger laps the jumps. “As of 2000, this was all veg­e­tated,” Maki says. “There was one sin­gle­track through here.”

Maki is dressed in a black ‘Don Vi­vants’ jersey, flu­o­res­cent-yel­low arm and leg warm­ers, and white socks with red polka dots. The son of World War II im­mi­grants—his fa­ther is Ja­panese, his mother Ukrainian—Maki grew up rac­ing cross coun­try and get­ting lost in the Don. He’s worked in bike shops since he was 16, in­clud­ing the last 15 years at Cy­cle So­lu­tions, where lo­cal bankers buy high-end Santa Cruzes and fete their clients in the Don in­stead of on a golf course. Ac­cord­ing to long­time builder and out­spo­ken ad­vo­cate Ti­mothy Charles, aka the Don­fa­ther, “No one knows the Don bet­ter than Maki.”

We con­tinue our ride along the chain-link fence and sewage plant, in­hal­ing a pu­trid smell that is part hu­man fe­ces and part squir­rel car­cass hang­ing on a tree branch at nose level. Dig­ger bails soon af­ter that, de­cid­ing his dirt jumper is not the right tool for this mis­sion. Maki, whose quads look like con­crete col­umns, cleans a tech­ni­cal sec­tion over lad­der bridges and rock­rolls be­fore top­ping out next to a ce­ment fac­tory at a plateau called the ‘Dooba­to­rium.’ Later, we pass the Trump Jump, or at least its rem­nants. It was built over 18 months, shortly af­ter an­other trail had been ripped out, to “Make the Don Great Again.” It lasted about a month be­fore city of­fi­cials ap­par­ently de­cided a 20-foot gap jump onto a nar­row, tree-lined runout was not li­a­bil­ity-friendly.

“Let’s duck down here,” Maki says at a junc­tion. “There’s a new trail that’s re­ally pri­mal.” We fol­low him through an Ewok forest and even­tu­ally up a se­ries of the tight­est switch­backs I have ever rid­den—built out of ne­ces­sity to max­i­mize the lim­ited land—on a trail called Climb­maxxx. We pass a half-buried shopping cart and lean into berms re­in­forced by a ve­hi­cle tire, logs and con­crete slab. At one point I think I glimpse a de­ceased toaster oven peek­ing out of the ground, but I can’t be sure. The brief de­scent ends at a gi­ant boul­der that thrusts rid­ers to­ward a canopy of leaves above, named—what else?— the Ejac­u­la­tor.

Dur­ing a pee break, I tell Maki that I re­cently vis­ited a trail net­work that was funded by more than $600,000 in grants and do­na­tions. “That’s funny,” he says. “These trails were built on two cool­ers of beer and a lot of time and sweat.”

Even­tu­ally Maki leads us to the east fork of the Don River, aka the East Don, where trails re­main more rugged than in the Main Don. We ride Kitchen Sink, so named for the kitchen sink that some early reg­u­lars found along the trail, caus­ing one to ex­claim, “This trail has ev­ery­thing and the kitchen sink!” The warm, forested rim gives way to a bona-fide jun­gle, then

a cool bam­boo forest where we weave be­tween stalks along the river. I hear some­thing flap­ping and glance over to see dozens of 20-pound Chi­nook salmon spawn­ing in six to eight inches of what looks like glacier wa­ter. I feel like I am 100 miles from a city—or 1,000.

“Do people swim in the Don?” I ask Maki.

“I wouldn’t rec­om­mend it,” he replies, and soon I will find out why.

Rarely does a climb in the Don last longer than 100 ver­ti­cal feet, which is about how much we punch up to a perch un­der or­ange fo­liage high above a gor­geous bend in the river. The breeze blows and Chi­nook flap as we look out over a fall forest, high-rise apart­ments in the dis­tance. When I booked my trip to ride in Canada’s big­gest city, I did not ex­pect to be phys­i­cally worked and gap­ing at the nat­u­ral land­scape, but sud­denly I am.

“This is my fa­vorite place in the Don,” Maki says, break­ing the si­lence. It’s easy to see why.

We pedal on to Mo­town, a noo­dle of dirt that snakes through a jun­gle of dog-stran­gling vine. A vi­sion­ary named ‘Quiet Steve’ built this trail over a pe­riod of three years. We can see the CN Build­ing—the fa­mous nee­dle in Toronto’s sky—through the trees. It oc­curs to me that we have en­coun­tered ex­actly one person since we en­tered the East Don two hours ago, de­spite blue­bird weather and es­ti­mates of 10,000 or more who ride the Main Don.

“You’d never know it,” Maki says, “but a few hun­dred feet from here, six lanes of cars are sit­ting in traf­fic.” BE­FORE IT BE­CAME A RID­ING HOT SPOT, THE DON WAS A DUMP. People threw their trash down ravines, where a large home­less com­mu­nity re­mained for decades. The river is cleaner now, but at one point it ranked among the most pol­luted wa­ter­ways in North Amer­ica. Big flood events still cause sewage out­flow, wherein raw sewage washes into the river and Lake On­tario a hand­ful of times a year. But usu­ally the wa­ter is at least clear.

As the ravines cleaned, old so­cial trails lured rid­ers deeper into the Don—which is named af­ter the River Don in York­shire, Eng­land, it­self named for a god­dess of Celtic mythol­ogy. Other rid­ers built new trails, even­tu­ally cre­at­ing a net­work that at­tracts ev­ery­thing from 160-mil­lime­ter forks to car­bon hard­tails. Some of the most ex­pen­sive houses in Toronto back to the Don be­cause of its recre­ational ac­cess. Lo­cals think it’s right­eous that $12-mil­lion cas­tles share a back­yard with

low-in­come apart­ment build­ings.

The Don is home to a hand­ful of out­door or­ga­ni­za­tions, in­clud­ing the Wild­bet­tys, a women’s moun­tain-bik­ing club with 132 mem­bers and IMBA-cer­ti­fied ride lead­ers. The club’s of­fi­cial motto is: “We do it in the woods,” but you might also see: “There’s no bet­ter place to do it than in the Don.” While cast­ing a wide net for sources, I heard about an­other group called the Don Vi­vants and ex­changed a few emails with a mem­ber named Ben Aylsworth, who also hap­pened to be one of the core trail­builders. I was try­ing to fig­ure out what, ex­actly, the Don Vi­vants were.

“This is a gang,” Aylsworth wrote. “And I mean gang. We are anti ev­ery­thing. In­ten­tion­ally lead­er­less. In­ten­tion­ally off the grid. But also pro ev­ery­thing. And we love the Don.”

I was pretty sure they wouldn’t kill us if we rode with them, but Aylsworth said they weren’t sure they wanted to let us in. Af­ter a group dis­cus­sion, they de­cided it was OK and Aylsworth apol­o­gized for his gruff first im­pres­sion. “I’m just pro­tec­tive of this lit­tle slice of urban heaven. What I do in the Don re­ally de­fines me and I think that’s true for most of us.”

Aylsworth grad­u­ally opened up and be­came a trusted source. A 45-year-old me­dia ex­ec­u­tive and fa­ther, he chased first de­scents in a kayak for years be­fore find­ing the Don and de­cid­ing it had what he needed, too, but was closer to home.

“My job is high stress, gi­ant events, lo­gis­tics, and I need a place where I can let that go, not be judged and do what­ever the hell I want to do,” he ex­plained. “I think that’s what the Don Vi­vants are for a lot of people. We’re in the heart of the fourth largest city in North Amer­ica, but no­body knows we’re here. We can kind of just let loose and run around wild in the Don. That’s im­por­tant for my life bal­ance.”

I found it ironic to learn that he and other lo­cals some­times feel in­se­cure about their prov­ince’s ‘On­ter­ri­ble’ rep­u­ta­tion as a rid­ing des­ti­na­tion, given what ex­ists in the Don. But those who know it, re­vere it. As Maki said: “I’m a simple person. This sounds weird, but some­one once asked me, what are your life goals? Well, I re­mem­ber think­ing when I was 17 years old—still in the hard­tail, V-brake era—I just want to be so good at rid­ing the Don that people know who I am just be­cause I ride the Don.”

Since the Don is mostly owned by the city, which is short on re­sources like every city in North Amer­ica, it sees al­most no pub­lic main­te­nance. But lo­cal builders say it is not un­com­mon for trail users—es­pe­cially run­ners—to give them money for ma­te­ri­als and tools. One builder, who wished to re­main anony­mous, said a fe­male trail run­ner once jogged to the ATM, with­drew $150, ran back to hand him the cash, then con­tin­ued on her way. An­other sent $200 to him via email. He has no idea who they were, but he tracks how the money is spent on a spread­sheet.

THE DON IS NOT THE ONLY PLACE TO RIDE IN TORONTO. Trails and cul­ture abound in ravines and open space across the city, like at the renowned Sun­ny­side Bike Park and in Eto­bi­coke Creek, where rab­bits dart across wa­ter­front sin­gle­track and graf­fiti un­der the Queen El­iz­a­beth Ex­press­way re­minds

ev­ery­one to “Fuck ’em. Do you.” Some in western Toronto think the Don gets too much credit, but there is no deny­ing it’s the epi­cen­ter. This is also why it re­mains a del­i­cate topic in in­ter­views. Lo­cals have been try­ing for years to move past their don’t-ask, don’t-tell stand­ing with the city, since they fear deep down that the trails could one day be shut down or dumbed down—or they could get in trou­ble for build­ing more.

But their ef­forts have al­ways been sti­fled by bu­reau­cracy, as well as a lack of moun­tain-bik­ing knowl­edge or in­ter­est at City Hall. Lately there is new blood and re­newed op­ti­mism, how­ever. Ian Gi­rard, 34, the in­ven­tory man­ager at Sweet Pete’s bike shop and a Don Vi­vant, is one of six people in­volved with launch­ing the Don Val­ley Trails As­so­ci­a­tion. Its man­date is still “loosely de­fined,” Gi­rard says, “but ba­si­cally it’s to pre­serve, main­tain and, I want to say ex­pand, but it’s re­ally not an ex­pan­sion be­cause it’s al­ready there. It’s more to pre­serve it.”

To find out where the gov­ern­ment stands, I met city en­vi­ron­men­tal spe­cial­ists Karen Sun and Mike Halferty one af­ter­noon at Crothers Woods. Each grew up in Toronto but had no idea the Don con­tained such a bounty of trails—in ad­di­tion to beaver, ot­ters, mink, deer and coy­otes.

When asked whether the city is in­ter­ested in le­git­imiz­ing the net­work, Halferty said yes. “The us­age is there. The jus­ti­fi­ca­tion is there,” he said. Sun, stand­ing next to him, added: “We would love for our rec staff to be run­ning moun­tain-bik­ing clin­ics on these trails. They haven’t be­cause they don’t know how to. You have to un­der­stand, moun­tain bik­ing is cut­ting edge in the eyes of the city. Our parks staff, if they can’t drive a truck to it, they’re not re­ally in­ter­ested in go­ing in there.”

Nev­er­the­less, city of­fi­cials of­ten find them­selves caught be­tween Don trail users and rail­road work­ers, who run trains through the Don. “We re­cently got a call from Metrolinx ask­ing if we have any con­tacts in the moun­tain-bik­ing com­mu­nity, be­cause ‘they keep cut­ting down our fences,’” Sun said. “And be­fore that, a lo­cal moun­tain biker asked me if I had any Metrolinx con­tacts be­cause ‘they keep putting up fences.’”

Five years ago, the city drafted a Nat­u­ral En­vi­ron­ment Trails Strategy to ad­dress the es­ti­mated 240 miles of trail on its land that it didn’t build and doesn’t manage. “I think what it comes down to,” Halferty said, “is the city’s li­able for any­thing that hap­pens on their land, re­gard­less of whether it’s sanc­tioned. So we might as well have good trails rather than shitty trails.”

To that end, when I asked Aylsworth why he was OK be­ing iden­ti­fied in this story as a builder, given that the prac­tice is tech­ni­cally il­le­gal, he said: “I don’t know. Maybe it’s a mis­take. But I also feel like the city knows that we’re here and they know what we’re do­ing. And we’re get­ting to that point where maybe we shouldn’t pre­tend that this isn’t hap­pen­ing and we shouldn’t pre­tend who’s in­volved.”

It did not seem like change was im­mi­nent last fall, but the dy­namic had also come a long way from yes­ter­year. “The city moves slowly be­cause it’s big,” Sun said. “You don’t want things to move too fast. If the glaciers move too fast, ev­ery­one dies.”

“But once they get rolling,” Halferty said.

“Yes,” Sun agreed. “Once they get mov­ing, big things get done.”

IT IS HARD TO IMAG­INE THE DON AS A LE­GIT­I­MATE RID­ING ZONE, with trail signs and kiosks and rules. It al­most feels sacro­sanct, like putting high rises in Yel­low­stone. But un­til some sort of move­ment oc­curs with the city, ev­ery­one tries not to think of it and sim­ply rides.

We meet the Vi­vants just be­fore dusk be­hind Loblaws. I’m still beat from rid­ing five hours with Maki this morn­ing, but it quickly be­comes ap­par­ent this will not be a ham­mer­fest, as some of their Thurs­day-night rides are known to be­come. The crew sizes us up like fish in a bowl. There is the bearded, red-tank­top-wear­ing Bos­nian Alen Zukanovic, 39, who im­mi­grated to Toronto in 1995 to es­cape the civil war in Sara­jevo; he came up with the name Don Vi­vants. I also meet Mikester, the old­est rider here at 62, who re­fuses to give his last name and de­scribes the Vi­vants as “a beer-drink­ing, pot-smok­ing club with a cy­cling habit, with doses of an­ar­chism, Satanism, and a big dash of com­mu­nity ser­vice.”

We set off down the hill en masse, fol­low­ing Aylsworth and a few oth­ers to the flats and even­tu­ally the Dooba­to­rium. We ride over an iron­ing board on our way to Garbage Cow, a faint trail through the woods that ev­ery­one loses at least once. At the top of a par­tic­u­larly punchy switch­back, Zukanovic pulls down his chamois and shakes his pale cheeks in ev­ery­one’s face, yelling, “You got it! Yeah!

Yeah! Yeah!”

Af­ter a cou­ple of hours in the forest, we head to a lo­cal brew­ery, grab a few cans of beer, and con­tinue to a bon­fire down by the river, at a site I have only heard de­scribed as “the Rocket” (I will learn later that it’s also known as the Stunt Camp, or Camp Campy Camp, for­merly home to 80 feet of skin­nies and a 6-foot drop called the ‘Dona­conda’). When we pedal out of the bush and into the clear­ing, I be­hold a mis­sile-shaped pro­jec­tile that is sur­rounded by Vi­vants and belch­ing or­ange em­bers to­ward the sky.

Aylsworth and Zukanovic are hang­ing out next to the world’s largest wire­less speaker, which 12 of them bought for $1,200. Cup­cakKe’s “Spi­der-Man Dick,” a raunchy hip-hop num­ber, blasts through the clear­ing. Right af­ter they bought the speaker, Aylsworth says, they held a ’90s rave in the Don and only an­nounced it on In­sta­gram. A bunch of Vi­vants DJed sets in dif­fer­ent lo­ca­tions, which were sup­posed to build up to­ward a pro­fes­sional DJ’s cli­mac­tic set. But he crashed on his way to the Rocket and broke his thumb. The Vi­vants also do a Hal­loween ride and the an­nual Don-a-thong, which amounts to 20 guys fly­ing through the forest in ba­nana ham­mocks.

“We’re all just chil­dren trapped in men’s bod­ies,” Aylsworth says at the fire.

To which Zukanovic adds, “We’re look­ing for some­thing that’s miss­ing in our ev­ery­day lives. This is why, if any of our friends or family say, ‘Are you busy on Thurs­day night?’ I have to say, ‘I’m sorry, but Thurs­day nights are out. Un­less it’s rain­ing. Then we can see.’”

I float around the gath­er­ing, chat­ting up var­i­ous Vi­vants. Among them: Michael Nazwaski, the youngest Vi­vant at 17, who has to be home by mid­night. ‘Naz’ has been keep­ing up with Maki in the Don, which qual­i­fies as a big deal in this cir­cle, though Maki still treats him like a lit­tle brother. Mikester si­dles up at one point and says, “A lot of the builders are here. These guys are gods. Hon­estly, I would do any­thing for them.”

Be­fore long some­one in­tro­duces me to Ti­mothy Charles, and the Don­fa­ther and I back away from the fire to talk. He is dressed in a plaid flan­nel shirt and jeans, which is about as for­mal as he gets. When I’d asked the Vi­vants why they call Charles the Don­fa­ther, one of them joked, “Be­cause he likes it.” I can see that as we talk, but his king­pin role is also ev­i­dent. He started rid­ing dirt bikes in the Don in the ’70s and first ped­aled it in 1981. “I’m the orig­i­nal bad boy down here, dude,” he says. “You can men­tion my name any­where you want. But I’m just a cit­i­zen.”

Around 2005, the Don­fa­ther, who is 54 and works as a gen­eral con­trac­tor, formed an in­for­mal race team called the Don­rats, ba­si­cally the pre­cur­sor to the Vi­vants. For nine years, he never missed a Tues­day- or Thurs­day-night ride. He’d grown up rowdy, once jump­ing 13 kids off a ply­wood ramp in the school­yard, and spent part of his ado­les­cence in Santa Cruz, where he learned the mean­ing of flow. “Just imag­ine your­self in­side a gi­ant teacup, and you’re just liv­ing in there,” he says. “That’s been one of the great­est joys of my life.”

A trio of new­com­ers emerges from the bushes, and the Don­fa­ther ush­ers them into the cir­cle. “Hello, hello, wel­come!” he says.

The Rocket, which is ac­tu­ally an old metal duct that they con­verted to a wheel­bar­row to use while build­ing trail, then aban­doned at Camp Campy Camp to an­chor their par­ties, lights up the night every few sec­onds. The Don­fa­ther goes on.

“My vi­sion of what a trail should be,” he says, “is you should be able to ride it without hav­ing to pedal. I re­al­ize there are cer­tain re­al­i­ties with that; we’re not in Whistler. But that’s the con­cept. And I love to fly, OK? Hu­mans are fightin’, flyin’ or fuckin’, let’s face it. I fly, baby.”

The party con­tin­ues un­til 1 a.m., when only four of us re­main. The Rocket has long since sim­mered to a faint or­ange glow. Dig­ger and the Don­fa­ther are ready to go home, so we all trudge through the bush and out of the val­ley where the se­cret re­mains.

Cap­tain’s or­ders: Matt Mor­rish takes five at the shop.

Above: Matt Mor­rish arcs past old car tires, the former trash re­cep­ta­cle now boasts berms. Be­low: Sleeves: op­tional. Bot­tom: The Wild­bet­tys proudly call the Don home.

Top left: Camp Campy Camp is all about good times for the Don Vi­vants. Top right: 12 people at $100 each = the world’s largest por­ta­ble speaker. Bot­tom: It could be a serene au­tumn set­ting in a re­mote, quiet forest but no, Mor­rish cor­ners ca­su­ally within a city of 6 mil­lion.

Carte diem: When life gives you a dump, build trails.Toronto gets it.

Al­ter­na­tive trans­porta­tion.

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