The Toughest Golf Courses in Westchester That You Can Play-Pound Ridge is #1

Pound Ridge Golf Club, tough and unique to the Westchester golfer

By Dan Murphy

In September of 2020, while still under COVID lockdown, Westchester golfers watched Bryson DeChambeau win the US Open at Winged Foot Golf Club in Mamaroneck.  As I watched the event, I realized and remembered how difficult Winged Foot was, and how it was truly the toughest course to play in Westchester.

Winged Foot’s West Course has consistently ranked in the Golf Digest Top 10 in the United States, and has hosted six US Opens, the first won by Bobby Jones in 1929, cementing the legend of Winged Foot.  The East Coast is also a top 100, and both are among the legendary Golf Architect A. W. Tillinghast’s greatest designs.

But most of us can’t play Winged Foot, unless we find a member to get us out, or if we pay $750 for a charitable golf outing at the club. And for those who don’t agree with my #1 pick of Winged Foot in our area, (Golf Digest always has it as the only Westchester club in the top 10), then your local club, be it Siwanoy, or Fenway, or Sleepy Hollow, or Croton National, is also difficult to get onto and play for non-members.

My next thought while watching Bryson win at Winged Foot was, what are the toughest courses that you can play, in Northern Westchester? My pick for the toughest challenge is Pound Ridge Golf Club, which was recently ranked by Golf Advisor’s 2002 as the 7th toughest golf course in the US, and #6 in Golfweek’s “Best Courses You Can Play in New York” for 2020.

Opened in 2008, In a region filled with classic layouts, Pound Ridge provides golfers with a refreshing and modern course design option. Dye’s signature design elements ¬– dramatic mounding, rhythmic routing, and subtle deception, abound at every hole.

Pound Ridge is the only golf course designed by Pete Dye in New York State. Dye has also designed Kiawah Island in South Carolina, which will host the PGA Championship on May 20-23. It is a unique golf course for any Westchester golfer to play, making it a must on my list every year.

But there is a reason why Pound Ridge is on the toughest courses you can play list. It requires players to hit their shots in the right places and have your A game around the greens. If not then you will be breaking 100, which brings me to my other point.

Can you have fun and enjoy your round at Pound Ridge, or Winged Foot, while scoring 100+? I asked this question to Brad Worthington, Head Pro at Pound Ridge. Worthington also worked at Winged Foot years ago, and reveres the club to this day and agrees, its #1 in Westchester and the area. “Whenever you can get a chance to play a great course, you should try and challenge your game, and Pound Ridge gives you that chance. With five different sets of tees, you can pick one that suits your golf skills. Regardless of how well you play, you will enjoy the challenge.”

“Pound Ridge continues the undeniable legacy of the genius of Pete Dye to test all the clubs in a golfer’s bag while also enjoying the legacy of his wonderous designs,” says Darren Wang, managing partner of Pound Ridge Golf Club. “While our course is a formidable challenge from the back tees, we feature five additional tee box options for players of all abilities to have a great time away from the hustle and bustle of daily life.”

Shortly after Bryson won the US Open, I returned to Pound Ridge determined to break 90. Through 15 holes, I was on my way to my goal, keeping it on the fairway and not three putting. But the last three holes at Pound Ridge can break you, as they did to my scorecard. I triple bogeyed the last three holes to score a 94.

Pound Ridge is certainly worth a visit once per year, and likely, you will be back for more. Some honorable mentions in the Northern Westchester area.

Centennial Golf Club, Carmel. A 27-hole layout, designed by PGA Champion golfer Larry Nelson, offers a difficult layout, sloping fairways and large greens that can easily be three putted.

Mohansic Golf Course, Yorktown. This Westchester County course was my home course growing up and is as long and challenging as it was 30 years ago. The 9th hole plays almost 600 yards and requires three great shots to get on the green. If you can get home in 2 on this hole, reach out to me for your prize.

Two private courses in the area that are worth it if you can get on for a charity outing or with a member:

I-Anglebrook is private, non-equity club in Lincolndale, designed by Robert Trent Jones, Sr. on 240-acres purchased from Lincoln Hall in 1998. A great, difficult layout, and a real treat if you can get on to play.

II- The Stanwich Club, Greenwich. This is another course that I would place in the “play it if you can get out,” category. Very exclusive and a very difficult, with perhaps the most difficult, sloping greens that I have every played on. You better have your A-putting game with you if you can get on the first tee.

If you want your club to be highlighted, please email me at dmurphy@risingmediagroup.com. I will be making the rounds this summer and look forward to reporting on how the many classic Westchester golf courses are playing. In the meantime, check out Pound Ridge Golf for a tee time, 914.764.5771 or visit www.poundridgegolf.com.