If you’ve ever participated in a big-city marathon, you’ve had the thrilling—and vaguely postapocalyptic—experience of logging miles on vast avenues that are miraculously purged of traffic. There’s something to be said for creating this kind of unobstructed running environment. But if you’re like native New Yorker Joe DiNoto, 42, you might argue that having to navigate a city’s messy energy on foot is an opportunity to catch a glimpse of its soul.

In 2011, while working as a bartender in the Lower East Side, DiNoto founded the Orchard Street Runners, an organization that has become known for its unsanctioned races. (It hosts five to ten each year.) The events have no clearly delineated course. Runners are only obligated to reach certain checkpoints—how they get there is up to them. As DiNoto puts it, there are “obvious opportunities to take a shortcut and obvious opportunities to get lost.” Cutting corners is encouraged.

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Prominent OSR races like the OSRW10K, an event exclusively for competitive female runners, are invitation only—though DiNoto sometimes puts out a call for race entrants on social media. There are no medals or T-shirts, and the field is usually capped at around 30 runners, which might be why DiNoto hasn’t had any issues with the authorities. Prize money is minimal ($50 to $100), but invites are coveted by locals eager to prove what they can do outside of a conventional racing format. They’re drawn by the prospect of competition, and also, perhaps, by a desire for authenticity.

“There’s inspiration all over the place that you can apply to running to give it some kind of emotional connection,” DiNoto says. He would know. The courses for the OSR Bread Route Race Series—start time 2 A.M.—is based on routes that DiNoto and members of his family used to drive in the middle of the night to deliver orders from his grandfather’s bakery. That personal touch goes a long way.

“I think it gives people a sense of being part of New York,” DiNoto says of the OSR events’ illicit appeal. “It’s the New York that everybody was drawn to, the New York that’s fading away.”