“Wheelies for Hire”: Gloucester’s Teen Bike Gangs Pivot to Tourism

By J.B. Fitzsimmons | Gloucester Correspondent

GLOUCESTER — In a turn that no one — least of all the city administration — saw coming, the very teenagers once scorned for popping wheelies in the middle of Rogers Street traffic have now become Gloucester’s newest and most ironic startup: Bike Taxis for Beach Tourists.

The teen bikers, once the focus of angry Nextdoor rants titled “Menace on Two Wheels!!!”, have now turned their skills into a beach-side side-hustle. Their pitch: a five-dollar back-pegs ride down to Good Harbor Beach, bypassing Gloucester’s recently-infamous $45-a-day parking fee and giving your sunscreen-slathered thighs the wind-in-your-face thrill of childhood irresponsibility.

“Why would anyone pay $45 to park when I can get them there in six minutes and a near-death experience?” said 15-year-old Caeden Williams, while adjusting his chrome pegs and donning a vintage Red Sox cap backwards for aerodynamic efficiency.

Armed with Bluetooth speakers blasting 2010s rap and a frightening disregard for lane divisions, the teens have cornered a market that the city never anticipated: tourists sick of being gouged for parking and willing to take a gamble on an unregulated, wheelie-based form of transit.

“I didn’t know if we were going to make it or end up through a windshield,” said Rachel Greenbaum of Brookline, who rode clutch on a bright green BMX with a basket full of towels and iced coffees. “But honestly, $5 versus $45? I’d do it again.”

City officials, meanwhile, are scrambling to respond to what Councilor at Large Jason Grow described as a “wildly illegal yet weirdly efficient” transportation model.

“Do we want teenagers running an ad hoc rickshaw service? Of course not,” said Grow. “But on the other hand, if these kids are going to be swerving between cars anyway, they might as well lighten up the beach traffic while they’re at it.”

A task force has been formed to determine whether the bike-taxi revolution violates public safety ordinances. Meanwhile, police have been told to “monitor the situation,” which in practical terms has meant watching TikToks of wheelie stunts and pretending to take notes. 

The biker teens show no signs of slowing down. In fact, they’re already planning to expand their services to include towel-carrying, beach cooler delivery, and even an after-dark ride-share option called “Glow Up Transport” featuring neon spoke lights and portable disco balls.

Some residents are impressed. Others are simply resigned.

“Just wait till they start charging surge pricing on weekends,” said Thatcher Road resident Pete LaFarge. “Then you’ll really see capitalism at work.”


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