Skateboarders shred Exchange Street during Portland’s Cobble to Cobble event
Portland’s Old Port becomes a skate‑city playground
PORTLAND – On a sunny Sunday afternoon, Exchange Street in Portland’s Old Port was filled with the hum of wheels, the clatter of metal and the cheers of a crowd that turned a city block into a giant skate park. The free, open‑jam event, called Cobble to Cobble, drew skaters of all ages and skill levels to the streets, celebrating the city’s growing skate culture.
The day began at noon, long before the first skateboard rolled onto the freshly waxed ledges. A 12‑year‑old named Henry Elias was among the first to line up, his eyes fixed on a series of cobblestone gaps. “My favorite part about skating is landing the trick,” he told reporters, already plotting a perfect 50‑50 kickflip that would send him spiraling over the uneven pavement.
Standing next to Henry were his friend Xavier Parkhurst, also 12, and a host of other skaters, all eager to test the newly installed custom ramps. The track was a mix of rails and ledges, set amid the historic brick facades of the Old Port. As skaters took turns, the streets echoed with “oohs” and “ahhs” – the soundtrack of a community in love with its sport.
The event was organized by Mocean, an independent Portland skate shop, and a handful of local vendors. The organizers set no hard rules, a fact emphasized by Nathan Keen, who calls himself the unofficial “Cobble to Cobble consultant.” “It’s very unofficial. There’s no rules as to what you can and can’t do on a skateboard, so everybody’s happy to just show up and do what they can and have fun,” Keen said as he filmed a segment for a local video.
A $5,000 cash prize was on the line, and the open‑jam format meant anyone could sign up, from seasoned veterans to first‑time riders. The day’s highlight came when Matthew Martin – a Portland native who moved to the city two years ago to help build the new municipal skate park – performed a “Wallie” trick that sent the crowd into a ripple of applause.
The event’s popularity grew each year. In 2025, it drew more than 2,000 attendees, and despite a weeklong delay this year caused by bad weather, organizers were confident the crowd would surpass that number again.
Not all the participants were male. Gabbi Perry, a roller‑skating enthusiast, rolled onto the street in a single pair of shoes, nervous but determined. “I was intimidated,” she admitted, “being a woman in a male‑dominated environment also made me a little nervous.” Yet the supportive crowd, led by the tight Portland skate crew, made her feel welcomed. “But the Portland crew is, like, one of the best crews of skaters I’ve ever met. Very welcoming, very encouraging,” she said.
The atmosphere was more than just a skating contest. Artists set up impromptu canvases, DJs pumped music, and local business owners sold vintage apparel and art along the curb. “It’s a big block party,” Keen said. “It could help fill in for the long‑gone Old Port festival and could be bigger than just skateboarding.”
The day ended with a sense of community. Kairi Stanbrook from Hull, Massachusetts, performed a trick that had onlookers cheering, while a 12‑year‑old from Hull, also named Kairi, added her own flair. The event left a clear message: Portland’s streets are not just a transit route but a canvas for creativity and a platform for all who love skating.
As the last skateboarder rode off into the evening, Exchange Street was still buzzing with the energy that only a true skate community can bring. Cobble to Cobble had once again turned a quiet downtown block into a celebration of skill, courage, and shared passion.
