Meet John “Johnny” O’Connor, snowboarding pro

Meet John “Johnny” O’Connor (left), snowboarding pro, from Windham, New York. Johnny is deeply connected to his hometown. He runs Jimmy O’Connor’s Windham Mountain Inn, a beloved local restaurant and inn founded by his late father, Jimmy, in 1970. Johnny carries on his father’s legacy. On any given night, you can find Johnny behind the bar, greeting locals by name, flipping burgers in the kitchen, or serving diners. He does it all, not out of obligation, but out of love.

“When my dad passed away in 2017, I knew I had two choices: sell the place or step up and keep it going,” O’Connor said. “It was a big change, but a rewarding one. I get to offer a space that people truly enjoy.”

For Johnny, preserving his family’s establishment means more than just running a business. It’s about maintaining a piece of Windham’s identity.

“It’s one of the last places in town that hasn’t changed in 55 years,” he said. “Change and renovation are great, but people appreciate having a spot that feels the same as it always has.”

Outside of the restaurant, Johnny is an avid snowboarder and skateboarder, passions that began early in his childhood. He learned to skateboard at age six and to snowboard at seven, starting on a small hill by his house, then a golf course, and eventually building his own jumps.

His love for skating began thanks to his sister. “She told me we should get really good at skateboarding,” O’Connor recalled with a laugh. “We just took off from there.”

That same drive led him to snowboarding. After receiving a snowboard video one Christmas, O’Connor became inspired to take the sport seriously, and by age 25, he had turned professional with Capita Snowboards.

“It was a dream come true,” he said. “It only happened through hard work, determination, and giving back to the community that supported me.”

That spirit of giving back inspired O’Connor to found the On Board Initiative in July 2024, a program offering free skateboard lessons to kids in Windham. His mission: to build a community skate park.

Thanks to donations from The Windham Foundation and The Community of Windham Foundation, O’Connor was able to provide skateboards, helmets, pads, and ramps for local kids.

The impact has been immediate and meaningful. “The kids talk about it all the time,” O’Connor said. “Teachers tell me it’s all they talk about at school. Their excitement has been the best way to get the community behind the idea of a skate park.”

The initiative also grew out of O’Connor’s connection to the Adaptive Sports Foundation, which teaches individuals with mental and physical disabilities how to ski, snowboard, and skateboard. He wanted to create a program that was inclusive and open to everyone, regardless of ability.

For Johnny O’Connor, community is everything. From running his family’s inn to mentoring the next generation of riders, his life reflects the values he was raised with.

“Community defines culture,” he said. “It’s what makes us human. We share traditions, learn, and grow together. If we all contribute to our communities, we’ll see ourselves and everyone around us grow.”

Thank you so much for visiting, Johnny!