Winding Hills Golf Club Montgomery NY is kind of a weird place, and I mean that in the best way possible. Most golfers in the Hudson Valley are used to two things: overpriced private clubs where you need a secret handshake to get a tee time, or "muni" courses that feel like playing on a dried-out parking lot. Winding Hills doesn't fit into either bucket. It sits right on Route 17K, and if you blink while driving toward Montgomery, you might miss the entrance entirely.
It’s an executive course.
That word usually makes "serious" golfers roll their eyes because they think it means a pitch-and-putt for kids. That’s a mistake. Honestly, if you go into Winding Hills thinking it’s an easy stroll, the narrow fairways and the relentless Hudson Valley elevation changes will absolutely wreck your scorecard before you even hit the turn. It’s a par-57 layout. That means you’re looking at twelve par-3s and six par-4s. No par-5s to be found.
But here’s the thing: you aren’t coming here to hit your driver 300 yards. You're coming here because your short game is probably a disaster and you need to fix it.
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The Reality of the Layout
Winding Hills was designed by Steve Esposito, and he clearly had a specific vision: make people think. You’ve probably played courses where you can spray the ball anywhere and still have a shot at the green. Not here. The course is carved out of heavy woods. If you’re off the line by ten yards, you are basically playing explorer in the brush.
The total yardage is somewhere around 2,599 yards.
That sounds short. It is short. But the greens are the real story. Unlike a lot of public tracks in Orange County that have flat, predictable greens, the ones at Winding Hills have these subtle, annoying tiers and slopes. You’ll think you have a straight uphill putt, and then the ball breaks three inches to the left at the last second. It’s frustrating. It’s also exactly what makes you a better golfer.
Most of the par-4s are "driveable" for long hitters, but it’s a trap. Hole 18 is a perfect example. It’s short, but there is water everywhere. You try to be a hero and go for the green, and nine times out of ten, you’re dropping a ball while the guys on the clubhouse deck watch you fail. It's humbling.
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Why People Actually Go Here
Let’s talk about the vibe. Winding Hills Golf Club Montgomery NY isn’t trying to be Augusta National. It’s approachable. You’ll see guys in hoodies, retired couples playing at a glacial pace, and teenagers trying to learn the game without getting yelled at by a marshal.
It’s also surprisingly affordable. In an era where greens fees are skyrocketing toward $100 even for mediocre courses, you can usually walk Winding Hills for a fraction of that. They have a massive fleet of carts, but if you’re physically able, you should walk it. The hills aren't a joke, but the scenery—especially in October when the leaves are turning—is worth the calf pain.
The Restaurant and Event Factor
The clubhouse is actually a bigger deal than the golf course for a lot of Montgomery locals. It’s called "The 19th Hole at Winding Hills," but it functions more like a community hub. They do a lot of weddings there. Like, a lot.
If you’re planning a round on a Saturday afternoon in June, check the schedule. You might find yourself putting while a bridal party is taking photos fifty yards away. It adds a weird, festive energy to the round, though it can get noisy. The food is standard pub fare—burgers, wings, the usual—but it’s done well. Better than it needs to be for a golf course, honestly.
Things That Might Annoy You
I’m not going to pretend it’s perfect. It’s not.
Because it’s a public executive course, the pace of play can be absolutely brutal. You get stuck behind a foursome of beginners who don't understand the concept of "ready golf," and suddenly your two-hour round turns into four hours. There isn't always a ranger on duty to move things along. You just have to accept it.
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Also, the drainage can be an issue. If it rained heavily on Tuesday, don't expect the course to be dry on Wednesday. The lower parts of the property tend to hold onto water, which means "cart path only" is a frequent reality. If you hate wet socks, check the weather report for the previous 48 hours before booking.
Technical Breakdown for the Gear Heads
If you’re wondering what to pack in your bag, leave the 3-wood at home. You won't use it.
Focus on your wedges and your mid-irons. You're going to be hitting a lot of 7-irons and 8-irons off the tees on those par-3s. The wind can whip across the open parts of the ridge, so being able to knock the ball down is a huge advantage.
- The Signature Hole: Hole 7 is usually the one people remember. It’s a drop-shot par-3 that looks easy but plays a club shorter than you think.
- The Turf: It’s typical Northeast bluegrass and fescue. It gets thick in the summer.
- The Practice Area: They have a putting green, but don't expect a 300-yard driving range. It’s more of a "warm up your swing" kind of place.
How to Get the Most Out of Winding Hills
If you want the best experience at Winding Hills Golf Club Montgomery NY, you have to time it right. Early mornings are peaceful. The fog rolls off the hills, and you can usually zip through nine holes before the crowds arrive.
Don't treat it like a championship test. Treat it like a skills challenge. If you can shoot par or better here, your iron game is legitimately elite. Most people who brag about their low handicap on big, open courses come here and struggle because they can't handle the tight windows.
The course is located at 1847 NY-17K, Montgomery, NY 12549. It’s literally right down the road from the Orange County Montgomery Airport. You’ll occasionally have small planes buzzing overhead, which is actually kind of cool and adds to the "hidden gem" feel of the place.
Actionable Steps for Your Visit
- Book Online: Their website is usually the most accurate for tee times, but calling the pro shop is better if you're trying to squeeze in a solo round.
- Bring Extra Balls: Seriously. The woods eat golf balls for breakfast. Even if you're a straight hitter, the narrowness of the back nine is unforgiving.
- Check the Wedding Calendar: If you want a quiet round, call ahead to see if there’s a big event scheduled at the clubhouse.
- Focus on the Par-3s: Use this as a "stat day." Track how many greens in regulation you hit. Since most of the course is par-3s, it's the best data you'll ever get on your approach accuracy.
- Walk the Front Nine: It’s the most scenic part of the property and offers a great workout without being completely exhausting.
Winding Hills represents a specific type of golf that is slowly disappearing: affordable, challenging, and local. It’s not fancy, but it’s authentic. Whether you’re a scratch golfer looking to sharpen your wedges or a local looking for a casual afternoon outside, it hits the mark. Just watch out for the water on 18. It’s deeper than it looks.