This article was originally published in the September 2023 issue of UltraRunning Magazine. Subscribe today for similar features on ultra training, racing and more.
It’s 2:45 a.m. and I’m doubled over in agony, trying to run up the pedestrian side of the Williamsburg Bridge. My lungs are on fire and I’m nauseous, clutching the railing as I pull myself forward, pausing only to throw up. I’m in serious trouble, less than 1 mile from the finish line of one of the most notorious, unsanctioned races in New York City, the OSR Bread Route Race.
For the last 6 miles, I’ve been running flat out, chasing over 200 of the fastest runners in the city through traffic, intersections and the motley cast of characters on the sidewalks in the middle of the night. We’re not running an official course—in fact, there is no course whatsoever and instead, we’re tracing “the former delivery route” of a baker, Frank DiNoto, who used to deliver bread on these very streets, nearly 50 years ago.
His grandson, Joe DiNoto, is now 46 years old and the founder of the Orchard Street Runners (OSR), the fabled New York racing organization, which is breaking new boundaries in ultrarunning, driving our sport to the urban, unsanctioned edge.
Earlier this year, I was invited by OSR to shadow the organization and its enigmatic leader, for two months of unsanctioned running.
RUNNING OUT OF BOUNDS
Though every major city in America is a patchwork of running clubs, it might surprise you to learn that NYC is home to over 200 running clubs. Whether the super-speedy Central Park Track Club, the Dashing Whippets, Black Men Run NYC, Harlem Run or the Bridge Runners, there’s a club for everyone in America’s most populous city.
However, no one can join OSR. “We’re not a running club or a running crew—in fact, we have no members,” DiNoto tells me over breakfast one morning on the Lower East Side. “We’re an unsanctioned racing organization with a Tuesday night threshold run.”
DiNoto founded OSR back in 2011, while between jobs as an architect and working as a bartender in NYC. After his shift ended late at night, he would take off on long, solo runs through the empty streets.
“I was pulled in by the energy of the streets late at night when the traffic is all gone,” says DiNoto, who wears a knit cap and an OSR pullover and comes across as an urban running shaman—anything but a running coach. “I never wanted anyone to see me out there while I was running. I didn’t want the headlamps or the reflective clothing… in fact, I wanted to be totally invisible.”
Captivated by the energy of the streets, DiNoto began designing unsanctioned races that would plunge top athletes into gritty New York running fantasies, races that would require a blend of fitness and urban street smarts. Races with no fixed routes, brutal cutoff times and very little prize money.
Over time, as word of OSR spread among urban runners—and dazzling neon-soaked images of OSR events spread on social media—the organization emerged as today’s leading urban running proving ground, drawing top runners from top clubs into DiNoto’s unique creation.
The OSR30
Just weeks later, I’m underneath the Brooklyn Bridge, standing in the second row at the starting line of one of OSR’s most challenging races, the OSR30. Unusual for OSR, this race is held in daylight hours, which is scant consolation because it’s a truly horrible March day, with driving winds, cold, biting rain and no letup in sight.
DiNoto is perched on a bike in front of us, arms raised, clearly pleased with how the day’s unfolding. I’m standing behind Maddy Nakada, the fifth overall American at this year’s Tokyo Marathon, and not far away is Travis Hawkins, a near-mythic OSR figure, who has won this grueling race four times. Today, however, he’ll have his work cut out for him because Greg Billington, a former Olympic triathlete, is here too, and some Dashing Whippets.
The OSR30 takes the urban adventure running trend to new heights. For this timed perimeter race, each runner must recruit their own dedicated bike escort, who helps them navigate 30-35 miles of urban running in 5 hours or less. Part traffic cop, part pacer and on-board GPS, bike escorts are key to success and must text DiNoto a photo of their runner arriving at five checkpoints or risk a DQ.
And then we’re off.
Everything’s a blur as a soaking wet mob of ultrarunners streak past me through the streets of Brooklyn. I’m jostled, charging forward blindly, lost in a pack of urban gazelles… as we hit intersections, runners peel off around the corners, taking their own routes.
I fight my way through a few blocks and then drop into a smoother gear as David Prince, my escort and a fellow New York ultrarunner, pulls up on his mountain bike, “You’ve got this, dude, same plan as before—straight up the guts.”
Once we enter Manhattan, our plan is to charge straight up the guts of Harlem and Washington Heights, taking the full brunt of the hills. It’s the most direct route to the tip of the city, checkpoint number three, the halfway turnaround, tucked among the hills under the Henry Hudson Bridge.
Greg Billington, 34, has the exact same idea, except he’s holding a 5:45-minute-per-mile pace and has managed to pass Travis Hawkins on the Upper East Side, “That’s one of the most challenging aspects of an OSR race,” Billington says, who currently runs for the Olympic Club in San Francisco. “Everyone takes their own route, so you never know where your competition is. After I passed him, I never knew where Travis was, so I just pushed myself the whole time.”
In the women’s field, Maddy Nakada was out in front for nearly the entire race, when Katarina Mayer, 24, a Dashing Whippet, surged into the lead at the Brooklyn Bridge, just 1 mile from the finish.
“My escort blew a flat at the Staten Island Ferry, at the final checkpoint, which was super stressful,” says Mayer. “I was surprised when I got up on the bridge and saw Maddy up ahead. I had no idea she was in first place, and didn’t figure that out till I saw the finish line and realized it was unbroken.”
With Prince pedaling at my side—and shouting down unruly cars—I ended up having a solid day, holding a 9:13-minute-per-mile pace through strong winds and biting rain, for 35 miles of running.
However, it was not good enough and I was DQ’d, coming in 22 minutes after the cut-off time.
TUESDAY NIGHTS
In many ways, OSR’s Tuesday night threshold runs serve as the heartbeat of the organization, which gathers every week in front of Regina’s Grocery on Orchard Street, just hours after DiNoto releases details of that night’s run on social media, with distances ranging from 6 to 14 miles.
When I arrive, I’m nervous—I’ve heard whispers about these threshold runs for years—but the OSR vibe is surprisingly mellow, even Bohemian. There’s generally a cast of 2-3 dozen runners on hand for each threshold run, whether it’s hard-charging NYC professionals looking for a rush, sinewy tattooed regulars or the running club drop-ins, the runners from various NYC clubs who want to put themselves to the test.
DiNoto, a joint tucked in hand, arrives alongside his bike and Corey Weiss, his girlfriend, a former Division 1 steeplechaser who also serves as an OSR race director. As music and the smell of food drift down Orchard Street, they chat comfortably with groups of runners perched at outdoor café tables, offering encouragement and a quick sketch of that night’s course.
At exactly 7 p.m., Ashley Gilberston, a longtime OSR runner and well-known NYC photographer who regularly leads threshold runs, steps out into the street, “I’ve had some drinks, so tonight I’m not leading the whole way.” And with that, he tears down Orchard Street with Corey Weiss and every runner chasing at his heels, while Joe shoots ahead on his bike.
Over the coming weeks, I would join OSR for three separate threshold runs and find an entirely new gear. Dashing amongst cars and tapping my knowledge of NYC streets, I’m surprised to discover that I can capably hold a 7-minute pace for runs as long as 14 miles.
THE OSR BREAD ROUTE RACE
Corey Weiss stands on the roof of a car shortly before 2 a.m. It’s late April and she’s shouting out directions to the over 200 NYC runners gathered here for DiNoto’s prized creation, the OSR Bread Route Race (OSRBRR), which he stages three times each year as a love letter to the city and his family.
Joe’s Grandfather, Frank DiNoto, was the founder of DiNoto’s Bakery, which thrived in the Bronx from the 1950s to the 1980s, ultimately having a fleet of 14 trucks, which Joe would ride in as a young boy, with his father and brother, getting his first taste of what the city was like in the wee hours of the morning.
“At 2 in the morning, when I put on this race, the streets are alive with the men and women who actually make this city work—the police officers, the bread truck drivers, the sanitation workers,” says DiNoto. “When they’re out there at those hours, they’re fighting to get home to their kids, to their families. It doesn’t matter if there’s a snowstorm or pouring rain, they’re out there every night. So, I wanted to bring people into this experience through running, and to honor our city and the sacrifices my family made for me to be here.”
For this particular race, DiNoto unveils four separate checkpoints just one day before the start, a distance of approximately 8 miles, carrying runners through a range of streets where the DiNoto’s used to deliver bread to hungry New Yorkers. Winners receive a $100 bill.
For my last OSR running experience, I arrived at the Bread Route Race transformed, a 55-year-old runner who recently traded distance for speed. For this final unsanctioned attempt, I’m determined to register my first-ever sub-7-minute performance, a pace I hope to hold for the entire race.
Though I see many familiar OSR faces, it’s the new ones that surge off the starting line, igniting fierce battles for urban supremacy as we chase down checkpoints, running into a bread delivery fantasy.
”The Bread Route Race fits the city perfectly—we’re the city that never sleeps,” says Amanda Gauthier, 27, who was the first-place female and runs for the Brooklyn Track Club. “I felt like a kid again out there on the streets, like I was playing in a game of manhunt. I didn’t know all the checkpoints, so my strategy was to keep close to the men and to follow them in.”
For the first 5 miles of this race, everything went to plan and I clocked four separate sub-7-minute splits. But just as I hit the Williamsburg Bridge, the unthinkable happened—I’m nauseous, dizzy, everything starts going black and I actually worry I’m having a heart attack. I stop dead in my tracks as a flash of OSR runners tears past me and I get sick, again and again as I pull myself up the bridge.
But in my mind’s eye, I see Joe DiNoto, the great urban run shaman of New York City, and I feel the heritage of the streets pulling at me, the story of the DiNoto’s and the countless immigrant families that built this city, so I surge onward, finding my final OSR gear as I tear off into the night.
(The author would finish with a 7:01 average pace and a grade-adjusted pace of 6:58.)