Colorful tie-dye style Woodstock Harley-Davidson mailbox with peace-sign logo in front of the dealership building.

WOODSTOCK HARLEY-DAVIDSON: WHERE NEW RIDERS ARE BORN

Words and images by Maxwell Barna

I’ve never been late to a dealership visit. Until I visited Woodstock Harley-Davidson.

In my defense, riding through the Catskills during the fall has been a bucket list item of mine since I first started riding. Hell, probably before that — since the first time I saw photos of how epic this place is when the leaves start turning.

Once I was finally there experiencing it, every single corner and bend begged to be stretched and carved, and deciding when to stop felt like deciding which finger I’d want to amputate if given no other choice.

I pulled in the night before, so I had a nice early start to a perfect late October morning. It was sunny and seasonably chilly, 43 degrees according to my weather app. After a good two hours just meandering through the popping orange, yellow, brown, and red leaves, stopping every now and again at a river overpass or scenic lookout, I realized that even with my early start, I was behind schedule.

  • The author’s Harley-Davidson parked on the sie of a two-lane road surrounded by yellow and orange fall foliage.
  • A woman working behind the counter at Phoenicia Diner.

After a “quick stop” at the Phoenicia Diner for breakfast (a must-stop if you’re ever up that way!) turned into a not-so-quick stop finishing one last cup of coffee and scraping every crumb off my plate, I finally set off down Route 28 for the 20-minute ride from the diner to Woodstock Harley-Davidson.

And even then, that 20-minute ride found a way to transform into a 30-minute scenic crawl.

By the time I pulled into Woodstock Harley-Davidson, I was a half-hour late. When I got inside and started apologizing to everyone, Bill Nugent, the owner of the place, waved my apology off as if he knew exactly what I’d experienced and was happy I did it.

Because he knows: the Catskills are an unbelievably special place, and Woodstock Harley-Davidson is at the center of its universe.

It was a Sunday and the dealership was closed, which usually doesn’t make the best time for a dealership visit. But this was no ordinary Sunday. This was graduation day for a small crop of H-D Riding Academy students, and Bill and the staff at Woodstock Harley-Davidson had invited me out for the ceremony.

THE CATSKILLS ARE AN UNBELIEVABLY SPECIAL PLACE, AND WOODSTOCK HARLEY-DAVIDSON IS AT THE CENTER OF ITS UNIVERSE.

  • Three Woodstock Harley-Davidson employees pose in front of the entrance to the dealership.
  • The exterior of Woodstock Harley-Davidson with fall foliage and blue skies.

Woodstock Harley-Davidson has been around for decades, but its story — and the people behind it — reach much further back.

The shop’s founder, Jan Dordick, opened the doors in Saugerties with her husband in 1975. Not long after, Jan’s husband passed away, leaving her as one of the only female Harley-Davidson dealers in the country at the time.

Nearly four decades later, in 2012, Bill Nugent took the reins, moving the operation to the Town of Kingston, right in the heart of the Catskills.

And Bill isn’t your typical dealer principal.

Before running Woodstock Harley-Davidson, he was already steeped in Harley’s past as an avid rider and collector who advised museums and private buyers on vintage models.

“Having the opportunity to own a dealership and expand the opportunity to help people buy not ‘just a bike’ but a way of life was very exciting,” he told me.

You can see that excitement all over the place. Every corner of the dealership carries a kind of reverence for Harley history, from the framed memorabilia to the lineup of motorcycles that sit on the showroom floor.

Vintage wall mural of a man riding a Harley-Davidson with a woman in a sidecar inside the Woodstock Harley-Davidson dealership.

Bill is also a history buff. So, to him, the past isn’t nostalgia as much as it’s a living thing that shapes the present. While we spoke in his office, he reminded me that in 1907, Walter Davidson himself rode through this very region as part of one of the earliest endurance competitions organized by the Federation of American Motorcyclists.

Another manufacturer had shown up with three factory riders and two chase cars full of parts, while Walter came alone. He pulled a Harley out of a New York City dealership, rode it up into the Catskills, and won the race outright.

He went on to win the next leg too, which ran from Brooklyn around the perimeter of Long Island and back again.

“Woodstock was right in the middle of that,” Bill said. “There’s something very special about New York Harley riders.”

That same spirit of determination, independence, and the sense of earning it is alive and well in Woodstock today. Bill told me that for years, the shop has drawn in visitors from all over the world.

“Woodstock is a destination,” he said. “People come here to see where it all began, to experience the freedom Harley represents. We have a large veteran community in our county, and we are proud to stand with them. As a 9/11 survivor, I fully understand the many nuances of ‘wind therapy.’ That’s not just a catchphrase, but a real antidote to life’s pressures.”

IN 1907, WALTER DAVIDSON HIMSELF RODE THROUGH THIS VERY REGION AS PART OF ONE OF THE EARLIEST ENDURANCE COMPETITIONS ORGANIZED BY THE FEDERATION OF AMERICAN MOTORCYCLISTS.

  • The interior of Woodstock Harley-Davidson showing motorcycles lined up for sale along with riding gear and apparel.
  • A Grateful Dead inspired t-shirt framed for sale that says New York at the bottom with the Harley-Davidson logo.

If the soul of a dealership comes from its people, Woodstock Harley-Davidson is rich in it. The staff all seem to be there for reasons that go beyond a paycheck.

People who, like Bill, live and breathe the culture. He smiled when he told me that customers are constantly stopping in just to say hello, and that people call the dealership every spring just to see if their limited-edition Woodstock Harley-Davidson T-shirts are on the floor yet.

That sense of community is part of what makes the new H-D® Riding Academy such a natural fit.

The dealership’s Riding Academy Manager and Events Coordinator, Antoinette Kaus, greeted me near the back of the showroom, where a table was set up with coffee, snacks, and the graduates’ certificates.

The group was small — just two new riders and their families — but that didn’t matter. For Antoinette, every new rider on the road is a reason to celebrate.

“This is our first year having the Riding Academy,” she told me proudly. “October twenty-seventh marked our one-year anniversary.” You could tell what it meant to her to see the students and their families gathered there, people who, just weeks before, had been struggling through their first clutch releases and slow-speed turns.

“It’s so rewarding to see each student pass the course and become more confident,” she said. “Some bring their families to the graduation parties. I’ve had students stop by just to visit. It’s amazing.”

Getting the program off the ground took time, but it was obvious that folks in the area were really excited to have a Riding Academy nearby. “We hosted a Ride Day event early on,” she said. “It was great to see people sit on a motorcycle for the first time. The excitement on their faces was incredible.”

  • Two H-D® Riding Academy students along with instructors pose with motorcycles in the parking lot at Woodstock Harley-Davidson.
  • Two H-D® Riding Academy students wearing helmets pose with motorcycles in the parking lot at Woodstock Harley-Davidson.

But there were hurdles too. New York State had delays in approving the Motorcycle Safety Foundation’s contract, pushing their first class start date from March to late May.

But even then, it was worth the wait, she said. “My hope for next year is to have more classes, more coaches, and start offering the BRC2 course. We already have past students excited to sign up.”

For the unfamiliar, BRC2 stands for Basic Rider Course 2, which is an intermediate course for riders who already have some miles under their belt.

It’s easy to understand why the program matters so much to Bill and his team. “Riding Academy is one of the best opportunities Harley dealerships have to introduce people to the brand,” he told me. “It’s not just a training program or a way to get new riders into the sport. It’s an invitation to the dealership. The anxiety of going to a dealership for the first time is completely washed away when students come here. They get to know the staff and see what we’re all about.”

THIS WAS EXACTLY WHAT HARLEY-DAVIDSON HAS ALWAYS BEEN ABOUT: CREATING COMMUNITY THROUGH THE ACT OF LEARNING TO RIDE.

  • H-D® Riding Academy instructor provides guidance to students as three staff members look on.
  • Two instructors award a student with a H-D Riding Academy certificate of completion.

That perspective is echoed by Tom Orlando, the dealership’s new General Manager.

His background spans decades in the powersports industry, having previously owned and operated a Kawasaki, Honda, and Suzuki dealership through the nineties. After years of consulting, he decided to slow down and plant roots somewhere that felt right.

“My wife and I love this area,” he said. “We honeymooned here years ago. It’s beautiful scenery, great motorcycle riding, and the area has a great vibe. Heck, it’s Woodstock.”

Tom’s enthusiasm for the dealership’s next chapter is contagious. “I believe this dealership has tremendous potential,” he said. “There’s a lot to build on here. With the new addition of the Riding Academy, plus implementing the sales processes I’ve used around the country, I know we’ll see drastic increases across all departments.”

His vision for Woodstock Harley-Davidson’s future blends tradition with innovation. “I plan to hold onto that iconic Woodstock vibe while capitalizing on the recent advances in retail, AI, and customer service,” he said. “We’ll become a pillar of the community by remembering that business is about people, not just money and products. And the Harley-Davidson brand takes that a step further, because it’s a lifestyle as well.”

As we spoke, the graduates filtered through, shaking hands and laughing with instructors, and enjoying some well-deserved graduation cupcakes.

It struck me that this was exactly what Harley-Davidson has always been about: creating community through the act of learning to ride. Here, in the shadow of the same mountains Walter Davidson once thundered through more than a century ago, people were still discovering what it means to feel that kind of freedom.

  • Looking over the shoulder of a student holding a “Stop on a dime” H-D Riding Academy certificate.
  • Two graduates of the H-D Riding Academy pose with instructors and staff after receiving their certificates of completion.

Outside, the air had cooled again. The sun was already starting to dip, and the light coming through the trees cast the lot in gold. While I was snapping some last-minute photos, I got to shake hands with the graduates and their families as they told me how excited they were to get on the road and start getting after it.

It was the kind of moment that makes you realize why dealerships like Woodstock Harley-Davidson matter and why our investment in H-D’s Riding Academy is so important. For many riders, this is the moment. The “eyes across the bar” moment, where they lock eyes for the first time with something they’re going to be in love with for the rest of their lives.

As I strapped my helmet back on and fired up the bike, I thought about how much of Harley-Davidson’s story is written by people like these. A small-town dealership tucked into the Catskills, run by people who care deeply about what they do, teaching a new generation how to ride. It felt right.

If you ever find yourself in the Catskills, stop by Woodstock Harley-Davidson at 949 State Route 28, Kingston, New York 12401, or give them a call at (845) 338-2800. Meet the crew, grab a coffee, and ask about the Riding Academy if you’ve ever thought about learning to ride.

Bill’s encyclopedic history of Harley-Davidson is absolutely fascinating to listen to, and you’ll find a team that knows what it means to start something new, and a place that’s been helping riders do just that since 1975.

  • An open hand holds a poker style chip with a Woodstock Harley-Davidson peace logo and phone number.

    WOODSTOCK HARLEY-DAVIDSON

    Kingston, New York

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