On Tuesday, August 1st, 2006, FINANCIAL POST Magazine published a wonderful article by Diane Peters. Much respect.


Toronto longboarders don't have the natural environments that inspire their kin in other parts of Canada. But when darkness falls, they turn the city's streets and empty parkades into adventure landscapes of their own.

Diane Peters, National Post
Published: Tuesday, August 01, 2006
Photography by Simon Willms

It's about 9:30 p.m. on a wet Wednesday night in late June, and a group of about 20 people ranging in age from their early teens into their 30s are sheltering under a bridge in downtown Toronto. They chat amongst themselves as the rain splashes down on the nearby streets, clutching oversized skateboards, known as longboards. Then, one man calls the proceedings to order. "You guys ready?" shouts Benjamin Jordan, whose pink bandana, mushroom of red hair and deep-seated reputation among Toronto longboarders makes him a beacon on this night. Jordan doesn't wait for an answer. He drops his board on the pavement and pushes off. The members of the group adjust their packs and follow without hesitation, trailing like a wave. The sight is almost ominous as they take to the streets, whizzing along darkened roads as fast as cyclists. "Is this a club?" one woman asks as the boarders flow around her on a sidewalk.

More of a loose community, actually. One that's come out on this crummy night for an event that's now a weekly ritual on the Toronto scene -- The Old Skool Night Shred. Over the next few hours, these longboarders will hit 10 parking garages in the city core. They'll bomb the empty ramps, drift along the curves and slide to dramatic stops on the smooth pavement, although gas-slicked puddles will turn even the simplest longboarding move into a soggy challenge tonight.

Whatever the conditions, it's hard not to see the appeal of riding these oversized skateboards. With lengths reaching up to 130 centimetres (the"shortboards" favoured by sidewalk tricksters are less than 100 centimetres) and large wheels that make them faster, they're just the thing if you like mixing your thrills with a bit of grace. Kids call them "skateboards for old people," as they're no good for tricks -- you don't need to know a kickflip from an ollie to ride with this crowd. Like surfboards for the street, longboards are built for cruising city pathways and flying down hills, slalom-style. And any boarder on any of the burgeoning scenes across Canada will tell you that the rush of carving out a long, clean ride wants for nothing.

But that's not all. Before long, they'll also start musing about the intangibles in terms that sound almost mystical. "It transforms things," one boarder will remark in a conversation a few days later. "Places become something new. You see an alley and it becomes something completely different."

And then they'll speak of the sport's sense of community. That's what's drawing Toronto longboarders out for this miserable night's shred. Many might have stayed in if it was a normal edition of the event. But tonight is special -- a send-off for Jordan. Three months ago, the 26-year-old photographer, a popular leader and innovator on the local scene, left Toronto for Halifax to join the Push for the Cure, a cross-country skate organized by three East Coast longboarders to raise money for the Canadian Breast Cancer Foundation. Tonight, he's in town on the tour's Toronto stop. When the Push ends in early October at Vancouver's Stanley Park, he plans to stay out west, where he's originally from.

The rain turns to a heavy downpour as Jordan's crew glides into a parking garage behind a hospital. Half the group crams into an elevator and rides to the top, but a security guard spots them when they get out. "Nice try," he shrugs. Back on ground level, Jordan decides to check out a garage next door, which no one in the group has ever tried. There are few cars and no security, so the group makes its way to the top. "This is a virgin garage!" Jordan hoots as he begins his descent. The boarders join in, weaving as they roll down, as if riding the coils of an apple peel.

Watching from the sidelines -- a non-boarder, I was told to bring my bike along so I could keep up -- it seems almost surprising that longboarding has managed to do more than eke out an existence in Toronto. Surfers in the cities of the West Coast first developed the sport decades ago, attaching wheels to their boards -- creating the first skateboards, in fact -- so they could practise when the water was too rough or too calm. For that reason, the sport has thrived in coastal cities such as Los Angeles, San Diego and, more recently, Vancouver. In fact, Vancouver is now home to numerous longboarding events, such as the annual Attack on Danger Bay, an official downhill race event with cash prizes, now in its fifth year, and the annual Seawall Cruise.

But these cities, and other Canadian locales where the sport has taken root, tend to be hilly places, or at least towns thick with bike paths. In stuffy, continental Toronto, boarders have had to adapt, taking their sport to the parking garages and bike lanes.

The longboarding community started growing here about 10 years ago, with Mike Brooke, today a 42-year-old father who publishes a successful skateboard magazine called Concrete Wave. In those early days, as longboarding was gaining traction on university campuses and ski towns elsewhere in the country, Brooke and a friend named Tom Browne would meet up at a downtown sports shop on alternate Sundays to cruise the city core and hit a hill or two. They called themselves the Metro Longboarders, and within a year were drawing an average of 10 riders to their sessions.

One of the regular Metro Longboarders was a young Benjamin Jordan. Jordan loved riding with the group, but he hated dragging himself out of bed in the morning, often hungover, to go for light cruises and talk gear. In the summer of 2003, he decided the Sunday sessions weren't dynamic enough for him: He wanted to hit serious hills, and he wanted the rush of riding with a larger group. Inspired by a leadership course he'd taken, he came up with an idea he called the "Board Meeting," a mass gathering of longboarders dressed in suits and ties storming Yonge Street. He scheduled the event for that September and publicized it with posters that read "Bomb Yonge Street like it's never been bombed before." To his surprise, 50 people showed up. He staged the Board Meeting again the following year, and the 2005 event attracted even more riders -- 100 in all -- plus media coverage and attention from the police.

A warning that the event was technically illegal did little to deter the group, however. By this time, longboarding was established in Toronto, held together not only by an increasing number of events, but also online discussion forums, which act like a glue for the community, as they are around the country.

It's hard to estimate how many longboarders ride Toronto's streets these days. Despite its counter-culture vibe, the sport attracts a variety of people. The youngest person at Jordan's goodbye shred is 13-year-old Luke, from Scarborough. But there are also people like Aubrey Iwaniw, the event planner, who works as a sustainability co-ordinator for the University of Toronto. Beyond this group, you'll find people riding well into middle age, with parents introducing the sport to their kids, or vice versa. Not everyone comes out for downtown events. Some ride alone, or join up with other groups around the city. But it's clear the ranks of enthusiasts are growing. Local shops can sell dozens of boards on a busy day, compared to stocking just a few five years ago.

In some respects, however, the Toronto scene has not evolved as much as it has in other cities. Vancouver's Attack on Danger Bay, for example, takes things to a whole different level, tempting competitors with prize money and attracting commercial sponsors. Likewise, Montreal's Top Challenge, an annual Labour Day competition for a variety of so-called "gravity sports," is a major event on the longboarding calendar.

With Jordan gone, the question of whether anything official develops in Toronto now rests with other community leaders, such as Iwaniw. A willowy 26-year-old and a natural organizer, Iwaniw has now taken over preparing the weekly night shreds and she'll be handling the planning and promotion for this year's edition of the Board Meeting, in September. She's also been active in introducing longboarding to new groups of people. Not long after discovering the sport in 2005, she began leading FUBU (For Us, By Us) sessions for women. After that, she started putting together introductory sessions so beginners could try the sport. It's great to see the interest, Iwaniw says, but she acknowledges that growing popularity can create problems at a practical level. Riders, for example, already get booted out of private garages. Last winter, one got slapped with a three-year ban from Toronto Parking Authority property. The presence of an increasing number of longboarders could lead to unwelcome attention from police or security guards.

While these are issues for the sport's enthusiasts, Iwaniw maintains an optimistic outlook. "I'd like to see people viewing the longboard as a choice for commuting and recreation. That's a good thing." And the potential for bringing legitimacy to the sport has other benefits. Toronto doesn't have official events, so boarders must travel to watch or participate in races and competitions. Broader recognition locally might improve the chances of staging events here, while easing the process of getting permits.

But these are matters for another day. Back on the streets, it's 1:30 a.m. and although the rain has long stopped, the riders are still wet and grimy. The farewell for Jordan is winding down. A few days later he'll cap it with a sentimental, but heartfelt, message to a long list of friends he posts on the Push for the Cure website. But for now, the remaining riders have stopped at Union Station, so those from suburbs can catch commuter trains home. The rest hop the subway -- or, as they did just a few hours earlier, adjust their backpacks, drop their boards and ride off into the night.