Designer: C.B. Macdonald/Seth Raynor (1913), Tom Winton (1920s, Additional holes), A.W. Tillinghast (1930, 9 Additional holes), Rees Jones (1992, Renovation), Gil Hanse/George Bahto (2007, Renovation)
Location: Briarcliff Manor, New York
History: Sleepy Hollow Country Club was founded in 1911 by wealthy New York businessmen including John Jacob Astor IV, William Rockefeller, and Cornelius Vanderbilt III. They enlisted C.B. Macdonald and his engineer Seth Raynor to design a course which opened in 1913. The course was immediately recognized as one of the finest in the country, but lost four holes in the 1920s to a landswap that were replaced by architect Tom Winton. In the late 1920s, another prominent architect A.W. Tillinghast added additional holes, making the course now 27. Today’s holes 1, 8-12, and 18 of the Upper Course were originally Tillinghast’s.
Still well-respected, Sleepy Hollow hosted the Champions Tour in the 1980s and 2002 U.S. Woman’s Amateur, but tree overgrowth and the conflicting styles of Tillinghast and Macdonald caused Sleepy Hollow to fall from the national limelight. This all changed in 2005 when the Club hired Gil Hanse and MacRaynor expert George Bahto to renovate the course, bringing back Macdonald’s style and clearing trees. The final product in 2017 brought new life to the 18-hole Upper Course and 9-hole Lower Course and is one of the most successful renovations of the 21st century. Sleepy Hollow hosted the 2023 U.S. Mid-Amateur and is highly ranked, earning the following awards:
- #77 Best Course in the World – Golf Magazine (2025)
- #66 Best Course in the World – Top100golfcourses.com (2025)
- #34 Best Course in North America – Top100golfcourses.com (2025)
- #52 Best Course in America – Golf Digest (2025)
- #40 Best Course in America – Golf Magazine (2024)
- #33 Best Course in America – Top100golfcourses.com (2024)
- #30 Best Classic Course in America – Golfweek (2025)
- #10 Best Course in New York – Golf Digest (2025)
- #10 Best Course in New York – Golf Magazine (2024)
- #10 Best Course in New York – Top100golfcourses.com (2024)
- #9 Best Private Course in New York – Golfweek (2025)
Conditions: 9/10, Sleepy Hollow is in great overall condition but isn’t quite as lush or manicured as some nearby courses in Westchester County.
Value: N/A, This is a private course.
Scorecard:
Tee Par Yardage Rating Slope
Black 70 6902 75.0 140
Blue 70 6630 73.2 136
White 70 6340 71.9 134
Yellow 70 5621 68.1 132
Red 72 5485 72.9 137
Hole Descriptions: I’ve been fortunate to play Sleepy Hollow several times now and must admit it is one of my favorite places to play golf. Situated about 45 minutes north of New York on the Hudson River, Sleepy Hollow is blessed with fantastic hilly golfing terrain and awe-inspiring vistas of the River that have been greatly enhanced by Gil Hanse’s renovation. The course is full of exhilarating shots and memorable template holes and features a fair degree of challenge without beating the golfer up. The par threes in particular are one of the best sets in golf culminating with the famous 16th and its tremendous views. I’ve yet to play Winged Foot at the time of this writing but think Sleepy Hollow is my favorite course in Westchester County otherwise, quite the statement giving the golfing depth in the region. This is a clear top 100 course in the World for me and is a course worth traveling for.
Your round at Sleepy Hollow begins next to the clubhouse with the 418 yard par 4 opener. Playing downhill on the teeshot, this is a fun hole with a crossbunker down the left at 275 yards and large tree down the right to protect the parallel 18th. A large mound on the right front of the green makes this a Leven template and creates a preferred angle from the left. This green otherwise features subtle mounds and slopes back-to-front, lined by bunkers left, long, and right. This hole doesn’t receive much attention compared to some others on the course but is a solid starter.
The 2nd serves as a transition hole, playing up the side of a steep hill and bringing you to the “Upper” part of the course. At 372 yards, this hole is the shortest par 4 at Sleepy Hollow but plays much longer due to this slope. You’ll need at least 190 yards to reach this fairway over a pair a bunkers and must avoid a right crossbunker at 250 yards and left one at 290 yards. This approach plays semi-blind at least a club uphill to a severely back-to-front sloped slick green lined by deep bunkers on either side.
When you arrive at the 2nd green, you get your first views of the majestic Hudson and stunning 16th, but don’t be fooled as you have a very tough hole to play. The 3rd hole is the first of four stellar par threes and is the toughest in my experience playing 172 yards over a valley. This is a very intimidating hole playing once again uphill towards a shallow green that runs both back-to-front and left-to-right. Steep slopes and five deep bunkers surround this green in all directions and bring big number into play here.
The 4th is another interesting hole as a straightaway 415 yard par 4. This hole features a generous fairway lined by rough and a solo crossbunker right and you’ll want to carry a plateau at around 260 yards or risk a blind shot into this green. This approach plays slightly downhill towards a long, narrow green lined by bunkers on either side. I would say this green is the trickiest on the course, running hard back-to-front and featuring a central spine down the middle that yields some very difficult pins.
At 435 yards, the 5th hole is a fantastic par 4 and is one of my favorites on the course. This slight dogleg right plays semi-blind over a plateau on the teeshot and initially doesn’t look like much. At about 230 yards, this fairway features a significant speed slot and is very generous, only lined by rough on both sides. When you crest the plateau in this fairway, this hole’s true beauty comes into focus with an infinity green in the distance and a gorgeous reveal of the Hudson in the backdrop. This elevated green is large, slopes back-to-front, and is lined by bunkers left and short on either side.
The 6th hole is the only par 5 on the front side and is a quirky dogleg right at 475 yards. Despite playing short and reachable, this teeshot demands your attention with thick forest down the right the entire way and a lengthy 230 yard uphill carry required to reach a second slab of fairway. Those who miss short will be left an awkward sidehill lie on a hill of rough and be blocked out while those who go long or left will likely find the 5th fairway. As soon as you reach the second slab of fairway, this hole turns hard right and continues uphill to a well-protected, back-to-front sloped green defended by bunkers short and right. I’m a big fan of the principal’s nose bunker strategically placed in the middle of the fairway about 100 yards from the green that greatly complicates a lay-up.
Sleepy Hollow’s 7th hole is another world-class par 3 as a downhill, 221 yard reverse redan. As much as I love the 16th hole, I think this is actually the best one-shotter here and is one of my favorites anywhere. Golfers will have to take less club with the severe downhill gradient and land their ball well-left of the pin to have it kick down towards the right. Seductive bunkering along either side of the green leaves a tough up-and-down but isn’t quite as bad as a miss long left.
If I had one slight critique of Sleepy Hollow, it would be that the tenor of the course changes a bit on the 8th hole, which begins the original Tillinghast stretch. These holes are not bad by any means and Hanse definitely put some Macdonald flair on them, but they are big and muscular compared to the rest of the course and definitely signify the toughest stretch. At 488 yards, the 8th hole is a monster par 4 playing straightaway with trees down the right and fescue left the entire way. Longer hitters can catch a left crossbunker at about 290 yards, but otherwise there isn’t much danger on this drive. As its name suggests, this green plays somewhat like St. Andrew’s famous Road Hole with a devilish front left potbunker and back-to-front sloped green with a false front. Par is a great score here.
The 9th hole is another challenging par 4 playing 424 yards as a slight dogleg right. This teeshot is a difficult one with OB right the entire way and a heavily sloped fairway lined by a bunker left at 260 yards. You’ll likely have an uneven lie on this uphill approach towards a back-to-front sloped green sitting on a pedestal and defended by deep bunkers on either side.
The 10th hole occupies the far southeastern portion of the property and is another fantastic par 3 at 168 yards. This hole plays downhill over water the entire way to a shallow green that slopes towards the water and features a devilish ridge running through the middle. A bunker left and hill of rough long make it so there are really no good misses here. I really like how this hole has two teebox options that play at varying angles.
Neither the longest nor tightest hole at Sleepy Hollow, the 11th has burned me several times and is a difficult par 4 as a 433 yard dogleg right. From the Black tees, this is an awkward and intimidating teeshot playing over water for the first 180 yards to a fairway that turns right around a rocky outcropping. Needless to say, a fade is the preferred play here. This approach is one of the toughest on the course towards a perched, back-to-front sloped green surrounded by deep bunkers on either side.
Once a stout Tillinghast par 4, the 12th hole was converted to a par 5 by Hanse and Bahto who created a brand new green about 150 yards to the left of the original. The longest hole at Sleepy Hollow, this 536 yarder plays as a dogleg left with a lengthy carry required to reach a generous fairway that bends left. A clever creek bisects this fairway about 75 yards short of the green and creates some interesting decisions on the golfer’s second shot. This green is also elevated and features a double plateau design, sloping overall back-to-front with a bunker right and steep slopes short and left.
The 13th hole marks a return of the Macdonald holes with an excellent uphill 408 yard par 4. This is a gorgeous straightaway hole featuring a generous fairway lined by forest right and a trio of blind bunkers down the left beginning at 250 yards. This approach runs at least a club uphill to a severely back-to-front sloped green defended by deep bunkers on either side.
From one of the highest points of the property, the 14th hole plays straightaway and downhill at 414 yards. Forest lines this fairway to the right and crossbunkers run across this fairway at 215 and 295 yards, but this hole is much easier than the previous few par fours. This approach continues downhill towards one of the best greens on the course, playing back-to-front with two tricky spines running vertically.
At 502 yards, the 15th hole is the longest par 4 on the course and the start of a brilliant and challenging finish. This hole begins with a fairly generous teeshot to a fairway that slopes left-to-right towards a crossbunker at 265 yards. While this teeshot isn’t difficult, most golfers are left a very long and blind second shot over bunkers to a splendid and huge punchbowl green. You won’t be able to see this green until you’re about 50 yards out, but the reveal here is one of the sweetest and most fun in golf.
Sleepy Hollow’s shortest hole is also its most famous in the 149 yard par 3 16th. This is one of the most photographed holes in the world (for good reason) and the excitement builds as you see it several times throughout your round. Playing slightly downhill, this is no more than a short iron to a large green surrounded by a moat of bunkers. This green is most notable for a central thumbprint but features some tricky and subtle slopes on the sides, making for some very tough pins.
The 17th hole is another long par 4 at 446 yards but plays shorter playing severely downhill the entire way. The downhill gradient and generous fairway inspire confidence in the golfer on this teebox but beware of numerous bunkers down the right that seemingly catch many balls due to the left-to-right tilt of this fairway. This approach plays a bit more level to a large, undulating green very well-defended by five bunkers surrounding it on all sides besides short.
Sleepy Hollow’s closing hole is arguably its most difficult playing back towards the clubhouse as a 426 yard par 4. Both the teeshot and approach play steadily uphill, making this hole play long. Dense forest lines the left side the entire way and thick rough lines a tight fairway to the right. This green slopes back-to-front and features a vicious false front and two very deep bunkers right. A par here will win the match more often than not.
General Comments: Sleepy Hollow is an active and thriving Club that has always been busy and bustling when I’ve played. Membership is fortunate to have a majestic clubhouse from 1893 that was once a Vanderbilt mansion and has rooms for lodging. Practice facilities include a practice green by the 1st tee and range between the 1st holes of the Lower and Upper Course. Walking with a caddie is encouraged and this is a taxing walk on a very hilly property.
Verdict: Newly rejuvenated by a landmark Gil Hanse renovation, Sleepy Hollow is once again one of the premier courses in America and is one of my absolute favorites. Golfers will love playing these fun template holes over a memorable and gorgeous terrain and an invite here is one to be savored.
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