Nestled in the heart of the Hudson Valley in Montgomery, New York, Winding Hills Golf Club has grown into more than just a golf course. Under the ownership of Christopher Ogden, the property has evolved into a destination that blends recreation, events, and community connection—while maintaining its relaxed and welcoming atmosphere.
From development vision to local destination
Ogden’s journey with the property began with a different goal in mind. “The original reason for purchasing it was for the residential housing development that we put in back there,” he said. Today, about 10 homes line the road behind the course. “If you continue down the road, there’s all housing down there.”
After purchasing the property, Ogden launched renovations in 2019 and continued through 2020, reopening during the COVID-19 pandemic. “Basically been running it since,” he said.
The early years required patience and investment. “Biggest challenges were just getting it off the ground,” Ogden explained. “It took two or three years to establish a name.” Building the event side of the business also took time, as bookings for weddings and large gatherings are often made 12 to 18 months in advance.
A course built for accessibility and skill
Winding Hills distinguishes itself as an 18-hole executive course, offering a different experience from traditional full-length courses. “It’s mostly par threes, so it’s a lot of short game,” Ogden said. “Our greens are very, very challenging. They have a lot of slope. They’re quite quick.”
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The shorter format makes the course more approachable. “You can play the whole course in about two and a half hours,” he noted, compared to five or six hours at larger courses. “So it’s not a big to-do.”
That accessibility draws a wide range of players, especially beginners. “I would say it’s more of your beginner golfer,” Ogden said. “We get a lot of people… just walk in, try to get a tee time and go out and play.”
At the same time, experienced golfers use the course to refine their skills. “A lot of people come here because they like to practice with their short game,” he said.
To keep the experience fresh, the course undergoes regular improvements. “We relocate our pins every couple of days to make it exciting,” Ogden said. “We’re constantly doing upgrades on the course.”
Drawing golfers from across the region
The club attracts players from throughout Orange County and beyond. “You could draw a radius around the course of probably 30 miles, and that’s your regular golfers,” Ogden said.
In addition to local visitors, golfers from northern New Jersey often make the trip. “They’ll travel up here to get their tee times,” he said, noting that courses in more densely populated areas can be harder to book.
Unlike many nearby clubs, Winding Hills remains open to the public. “Anybody can come and play,” Ogden emphasized, making it an accessible option for both new and returning golfers.
A versatile venue for events
Beyond golf, the club has become a sought-after venue for celebrations and gatherings. Winding Hills hosts about 70 weddings each year, ranging from intimate ceremonies to large-scale receptions. “We have what we call micro weddings… under 50, and then we have our full-size weddings… anywhere from 150 to 200,” Ogden said.
The venue also accommodates a variety of other events. “We do Sweet 16s, we do proms, we do birthday parties, baby showers,” he said.
Seasonality shapes the event calendar. Outdoor tented weddings dominate the warmer months, while smaller indoor gatherings fill early spring and late fall. During winter, activity slows due to limited indoor capacity.
Natural beauty and built challenges
A defining feature of Winding Hills is its scenic landscape. “The scenery here is gorgeous,” Ogden said. “We have rivers, we have ponds, we have views. It’s a very wooded course.”
The natural setting enhances both the visual appeal and the level of difficulty. “You have to kind of shoot around trees and stuff like that,” he explained, adding a strategic element to play.
Maintaining that environment requires ongoing effort. A full-time crew handles mowing, landscaping, and upkeep, with staffing reaching about 45 employees during peak season. “It’s a lot of work,” Ogden said.
Supporting the community
Community involvement plays a central role in the club’s mission. Winding Hills regularly partners with local schools and organizations for events and fundraisers. “We just did a charity golf outing… for the all-night graduation party,” Ogden said, referring to a recent event supporting Pine Bush students.
The club also hosts school-related sports functions and celebrations. “We work with the schools,” he said.
Younger players are introduced to golf through summer camps, which run for several weeks each year. “Very popular,” Ogden said, noting a growing interest in the sport among teenagers.
Looking ahead
While the club has already undergone significant improvements, Ogden remains focused on continued growth. “We’ll be continuing to do improvements on the course,” he said. One planned addition is rebuilding a putting green to provide more practice space.
For Ogden, the most rewarding part of ownership is the experience guests take away. “We like that everybody comes out of here with a positive feeling,” he said. “We try to be as accommodating as possible.”
From casual rounds of golf to weddings and community events, Winding Hills Golf Club continues to establish itself as a welcoming and multifaceted destination in the Hudson Valley.
