On April 10, Jon Stenning set out on what would become the most grueling, yet deeply rewarding, experience of his life — a solo, five-day, 512-mile cycling journey from North Scituate, Rhode Island to Washington, DC. While the main purpose of the ride was to raise funds for the Transgender Law Center and the National Parks Conservation Association (NPCA), the journey evolved into something far more personal. What began as a symbolic protest ride turned into a transformative experience, both physically and emotionally, highlighting the power of resilience, community, and self-discovery. Stenning, co-founder of RI’s inclusive cycling group It’s Just a Hill (IJAH), originally joked that he wanted to “flip off the Capitol Building,” but quickly realized that his ride could be a vehicle for real change. With support from his community and a growing online following, he raised over $5,700 (and counting) for the causes closest to his heart: protecting trans rights and preserving public lands. Despite months of planning, the ride didn’t go quite as expected, and that’s what made it unforgettable. From the start, the ride presented challenges. On Day 1, unseasonably cold temperatures — hovering in the 30s and low 40s — greeted Stenning and his father, who had planned to join Stenning for the whole ride. Unfortunately, his dad was forced to bow out before the first day was over due to injury. “We had breakfast together the next morning and made the decision that it was best I carry on alone,” Stenning said. The early emotional blow made the already taxing ride even tougher, but he pressed on, fueled by purpose.
The backroads of New York offered beautiful scenery, but Day 3 became a defining moment. He woke up to snow on the ground in New Jersey, and the first 25 miles were a mental gauntlet — sleet, snow-filled bike lanes, and drivers with little patience; riding in the road became the only option. A turning point came when he stopped at a local deli, where the owners offered him coffee, encouragement, and even latex gloves to wear under his cycling gloves. “That kind of support meant everything,” he said. Later, a bike shop not only charged his low derailleur battery and gave him snacks, but one employee, recognizing Stenning’s NBX jersey from his days at the University of Rhode Island, made a donation on the spot. But not all stops were as welcoming. In Trenton, NJ, he stayed at what he called “the sketchiest motel I’ve ever been in.” He wasn’t allowed to bring his bike into the room until he ended up ultimately placing it in the shower and deep-cleaning it himself. The room lacked toilet paper, and the door didn’t have a double lock, so Stenning wedged his bike against the door for extra security.
Flooded roads and reroutes marked Day 4, but the ride itself was smoother, spent rolling through scenic farmland in Pennsylvania and Maryland, and ending in Aberdeen. “People kept asking about the trip — it was one of the first times I felt like I could actually enjoy the ride,” Stenning reflected. Day 5 brought a sense of nearing the finish line, though riding through Baltimore proved frustrating, with bike lanes abruptly ending and inconsistent infrastructure. Once south of the city, things improved dramatically. The Anacostia River Park Trail led him into DC, where top-tier cycling infrastructure offered a smooth finish. But it wasn’t until he reached the hotel and embraced his wife that the emotional weight of the ride hit him. “I broke down, — in a good way,” he admitted. “I don’t give myself enough credit. I’m always living in the moment, maybe too much. But in that moment, I finally let myself feel proud.” The ride gave Stenning more than physical satisfaction. It brought mental clarity. “I’ve struggled with depression and anxiety. I don’t always love myself the way I should,” he said. “But holy shit, I did something I set my heart to and trained for. And I made it.”
Text messages from friends appeared on his bike computer throughout the trip, providing unexpected encouragement. “That meant the world,” he said. “It reminded me how many good people are out there.” Among his highlights were spotting over 30 bald eagles, visiting several museums — including the National Museum of African American History and Culture and the National Museum of the American Indian — and reflecting on how the outdoors shaped him. “I was an indoor kid growing up,” he said. “The outdoors give me mental clarity. It’s a place to disconnect. Riding for the sake of riding, now that’s something I’ll never take for granted.” In total, he covered 512 miles — more than the original 490-mile plan — due to reroutes and hotel locations. Every detail was researched in advance, from safe roads to nearby bike shops. “I was lucky, and pretty well prepared,” he said, though he admitted he should’ve packed warmer gloves. Stenning took the train back home — seven hours through much of the same path he had just ridden — and marveled: “I rode my bike all of this.”
While Stenning said he wouldn’t repeat that exact route (especially through Baltimore), the ride lit a spark for future bikepacking trips. “It was the trip of a lifetime,” he said. “To ride for something bigger than myself and actually enjoy it — it was a win-win.” The fundraiser is still open, with a new goal of $6,000. With over 110 donors already, Stenning plans to keep spreading the word through his “It’s Just A Hill Cycling Podcast” found on Youtube. His story is a testament to perseverance, vulnerability, and how powerful a bike, and a purpose, can truly be. •
To support the cause, text PEDAL4PROGRESS to 707070 or visit pledge.to/pedal-for-progress-a-ride-todc-for-change.
Artwork: Emily Boardman. Insta: @quahog-creative
