Andrew Singh Builds Hudson Valley Skate Culture with Connect Skateboarding

Andrew Singh grew up skateboarding in Beacon at a time when the Hudson Valley offered little in the way of infrastructure—or even basic guidance—for aspiring skaters. There were no skate parks, no local shops to anchor the culture, and no older generation to pass down knowledge. “We did not have skate parks,” Singh says. “We had no older people to really look up to…there was really no resources for us to learn and grow.”

What existed instead was a small, self-reliant crew—three or four kids figuring it out as they went. Singh was largely self-taught, learning through repetition, trial and error, and occasional trips to New York City, where a larger skate ecosystem took shape on the streets. “I had to travel all over the world and compete everywhere and just travel down to New York City like two, three times a week,” he says. “There was nobody up here teaching skate lessons.”

That absence—of mentorship, of infrastructure, of a visible pathway—became the foundation for what Singh is building now. His organization, Connect Skateboarding, launched in the summer of 2024, aims to create the kind of support system he never had. “I really wanted to grow the scene here in the Hudson Valley and give people a valid resource for everything skateboarding-related,” he says.

At 31, Singh occupies a transitional space familiar to many professional skateboarders. After years spent filming, competing, and traveling—“you wake up, you go filming with your filmer, you get footage for your sponsors”—the economics of the sport shift. “There’s a very, small handful of professional skaters that make a living off of skateboarding after 30,” he says. “Things start to slow down.”

For Singh, that shift has meant turning outward, toward community. Connect Skateboarding operates as a hybrid of instruction, outreach, and cultural organizing, with programs running through municipal recreation departments, public schools, and local partnerships across the Hudson Valley. Singh points out that while he has instructors assisting in the field, the operation itself is largely a one-man effort. “As far as operations, that’s all me,” he says.

The structure of a typical program reflects both pedagogy and intention. In a recent five-week after-school program at J. V. Forrestal Elementary, where Singh attended as a child, students began by designing their own skateboard decks—blank boards transformed into personal canvases. “They come in, they get to design their own graphic,” Singh says. “Then when they come in for week two, they have their own custom skateboard that they made.”

From there, the curriculum builds gradually: safety, stance, and how to fall; then the basics of pushing and balance; followed by incremental skill-building. By the final week, students are attempting turns and simple maneuvers. Along the way, there are side projects—like tie-dyed program T-shirts—that reinforce a sense of ownership and identity. At the end, the students keep their boards, leaving not just with a new skill set but the tools to continue.

The emphasis, Singh says, is not on producing elite athletes. “We’re not trying to train kids to be the next Tony Hawk,” he says. “We want them to have fun. We want them to feel confident in themselves—even if it’s taking a push and putting their foot on the board, they feel like they accomplished something.”

That focus on confidence is particularly visible in first-time participants. Some arrive eager; others are tentative, pushed into the program by parents hoping to pull them away from screens. “There’s a lot of nerves,” Singh says. “But we really do take pride in making sure that every kid feels safe and comfortable.”

If skateboarding once carried a reputation for rebellion—Thrasher magazine, anti-authority energy—that image has softened in recent years. Singh points to the sport’s inclusion in the Olympics, its presence in video games, and broader media exposure as forces that have shifted public perception. “It’s way more commercialized now,” he says. “That rebel image is starting to slowly die.” The fact that skateboarding now appears in school programming underscores the change. “How rebellious can it be if it’s in the schools?” he adds, laughing.

At the same time, the sport’s appeal has widened. While most Connect programs are youth-focused, Singh also works with adults—often parents of participants—who are curious about revisiting or trying skateboarding for the first time. For some, it’s a way to share an activity with their children; for others, it’s an alternative form of exercise. “It is a workout,” Singh says. “And there is a thrill to it that a lot of adults find.”

The broader skate landscape in the region is also evolving. Municipalities have begun investing in skate parks, a shift Singh attributes in part to increased visibility and to a growing recognition of skateboarding’s mental health benefits. “People are starting to realize that it’s not only positive for your physical health, but it’s positive for your mental health too,” he says.

Connect Skateboarding has already played a role in that expansion—Singh notes that Beacon is now getting a new skate park—and he sees that momentum continuing. His long-term vision includes opening a dedicated indoor space: part skate facility, part community hub, potentially with a small retail component. “I want to open up a space where we can run our own programs,” he says. “Have a little skate shop…just our own dedicated space.”

For a region that once offered little more than pavement and improvisation, that vision represents a significant shift. Singh’s project is less about elevating skateboarding into something new than it is about building the connective tissue that allows it to take root locally. “We started with nothing,” he says, reflecting on his own experience. “Now we’re trying to make sure the next generation doesn’t have to.”

On the Cover: The Mahican Bowl—Is It Art or Is It a Skate Park? | October 2020

Anne Pyburn Craig October 1, 2020October 1, 2020