Jon Cavalier
Jon Cavalier
Jon Cavalier
Jon Cavalier
Jon Cavalier
Sleepy Hollow Country Club
Scarborough, NY • Private
Sleepy Hollow Country Club
777 Albany Post Rd
Scarborough, NY 10510-2400
United States
Overview
In the mid-2000s, the late George Bahto, who had extensively researched the works of legendary architect C.B. Macdonald, partnered with Gil Hanse and partner Jim Wagner to remodel Sleepy Hollow Country Club, which consisted of 11 Macdonald-designed holes and seven added in 1927 by A.W. Tillinghast. The pair persuaded the club to allow them to rebuild the entire 18 in Macdonald’s style, reasoning that Tillinghast was well represented elsewhere in Westchester County (Winged Foot, Quaker Ridge and others), but Macdonald was not. The construction was done in stages, completed well after Bahto’s death in 2014. Thanks to Hanse, Sleepy Hollow now features some of Macdonald's “ideal holes," like the Eden, Knoll, Leven and Road holes that weren’t even part of his original design. And it has steadily climbed in our rankings the past few editions. Sleepy Hollow hosted the 2023 U.S. Mid-Amateur.
About
Awards
Ranking history:
100 Greatest: Ranked since 2019.
Previous ranking: 59th.
2025-'26 ranking (highest): 52nd.
Second 100 Greatest: Ranked from 2013-2018, including 101st in 2017-2018.
Best in State: Ranked Top 15 in New York from 2015-2016 & since 2019; Top 20 from 1995-1999, 2011-2014, & 2017-2018; Top 25 from 2001-2009.
2025-'26 ranking (and previous): 10th.
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Panelists
Ratings from our panel of 1,900 course-ranking panelists
100 GREATEST/BEST IN STATE SCORES
Shot Options
Character
Challenge
Layout Variety
Fun
Aesthetics
Conditioning
Reviews
Review
“Sleepy Hollow is a special place in the game of golf."
Read More2025
Review
“Special, iconic, beautiful, difficult are all adjectives to describe Sleepy Hollow CC. From the moment you enter the property, you know you're in for a round like no other. Great views, fast greens, wonderful conditions and a very welcoming staff make for an enjoyable day. It is a difficult walk but worth every step. Do not hesitate to say "yes" if offered the opportunity to play this C.B. MacDonald/A.W. Tillinghast Golden Age classic."
Read More2025
Review
“Fantastic golf course! The elevation changes make this a challenging walk and golf course with very few level lies. The views from the top of the hill out over the Hudson River are breathtaking. During the renovation, thousands of trees were removed to open up the course and give you broad views of the course and a true appreciation for the property it sits on. The variety of shots you need to hit, along with the precision required on the large, undulating greens, keeps you engaged for all 18 holes."
Read More2025
Review
“An amazing CB MacDonald course with spectacular views of the Hudson River. Playing this course in mid-July is a challenge as the heat / humidity makes for a difficult walk. The layout is fantastic especially on the back 9. My favorite was the punchbowl green on #15 followed by the par 3 16th thumb print. Amazing conditioning throughout coupled with outstanding service and a welcoming attitude make this a "must play" when in NY."
Read More2025
Review
“Immaculately conditioned C B MacDonald course with views of the Hudson River. Includes many of MacDonald's template holes."
Read More2025
Review
“Immaculately conditioned C B MacDonald gem on beautiful rolling property with views of the Hudson River. It displays some of MacDonald's famous template holes."
Read More2025
Review
“I can't think of two better holes with the great reveal when you crest the hill for the punchbowl green on 15 and then the par 3 16th thumb print. There is a uniqueness with the layout that makes this course great. Along with some amazing conditioning this is truly a gem."
Read More2025
Review
“Sleepy Hollow Golf Club is the often-cited example of a perfectly executed renovation. Take an incredible course, choked by trees, shrunken greens, that has been overly manicured and watered, and expand greens, enliven bunkers and eliminate thousands of trees to open breathtaking views. We’ve all seen hundreds of photos of the 16th green with its thumbprint and views of the Hudson River, the long rustic bridges connecting the 3rd, 4th, 15th and 16th greens, and the palatial clubhouse, but beyond those incredible places, Sleepy Hollow continues to shine brightly. I was wonderfully surprised throughout the round of other locations that stood out, the cadence between the 8th to 12th holes feel like a roller coaster that is careening down the tracks. The native area that the holes straddle adds just the right amount of visual juxtaposition to the perfectly conditioned fairways and greens. The combined green complex of 7 & 14 does a lovely job connecting both the front and back as well as the main paddock before starting the exceptional finish of 15-18. What ends up being a truly enjoyable course with tons of option and challenge is only belayed by the dearth of similar shorter length par-4s. Six holes are between 417-433 yards, and two more in the 440s. Comparing it to other golden-age masterpieces in the area, Sleepy Hollow’s lack of distance on the par 4s stops it from being a truly championship experience. With that being said, I thoroughly was smitten with Sleepy Hollow, it absolutely lived up to the hype created by its beauty. It was a challenging, fun, characteristic course with a ton of variety and options."
Read More2024
Review
“Spectacular views of the Hudson River, which provide a dramatic natural backdrop. The course thoughtfully integrates classic template holes, complemented by unique Par 3s, creating a layout that is both strategically engaging and visually captivating—a truly fun and memorable round."
Read More2024
Review
“The elevation changes, scenic views and unbelievable ground features make this a one of the top golf courses ever!"
Read More2024
