Upper Course
Scarborough, NY, USA
Sleepy Hollow is a storied enclave where championship golf meets Gilded Age elegance along the Hudson River. This classic, early 20th-century parkland design, sculpted from rolling Westchester County hills, demands strategic play and precise approaches to undulating greens. Originally crafted by the master hand of C.B. Macdonald, with later enhancements by A.W. Tillinghast and Gil Hanse, Sleepy Hollow challenges golfers with a variety of demanding doglegs and dramatic elevation changes. Although it hasn't hosted major championships, the club maintains a discreet reputation among those who appreciate the finer aspects of the game, and the historic setting. Sleepy Hollow’s membership, drawn from the New York City area's business and social elite, carries on traditions that predate the club's formal establishment. Legend has it that the land's previous owner, William Rockefeller, would invite friends for informal rounds, setting the stage for what would become a bastion of northeastern golf. And keep an eye out for the resident hawks, who are known to occasionally snatch a golf ball right off the green, adding an unexpected hazard to an already challenging round.
Ranked by CV ratings from golfers who've played this course. Positions are shown worldwide, by country, and by state; the Private column compares member-only and guest-restricted courses.
Best in World
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Best in USA
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Best in NY
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Golfers say Sleepy Hollow delivers a thrilling experience on dramatic terrain that traverses hills, canyons, rivers, and rocky outcroppings across a massive property. Most praise the routing and variety, highlighting the exceptional set of par 3s—particularly the photogenic 16th and the punchbowl 15th—as among the best anywhere, along with excellent template holes and wildly contoured greens that demand precision. Reviewers note the course plays extremely firm and fast with deep, penal bunkers and challenging green complexes, making it as difficult as any layout in the New York area, especially the demanding finishing stretch. The conditioning earns consistent acclaim, with several mentioning the Gil Hanse restoration has elevated the C.B. Macdonald design to top-100 status, and the stately clubhouse and welcoming membership add to the memorable experience.
9.2
260 players
Great
Very few experiences better than Sleepy Hollow. Conditions are spectacular, layout is historic, and the views are amazing. The history of the club is incredibly interesting and the old school style of the golf course really has stood the test of time. One of my absolute favorites.
One of the golf experiences anywhere. Amazing set of par 3s. Clubhouse amazingly cool (watch Friends and Neighbors). Lower course pretty awesome too….
Golf course is absolutely awesome and the logo is sweet
You’ve seen the pictures of 16 all over the internet, but the rest of the course is equally thrilling. Massive piece of property with an out and back routing that traverses hills, canyons, rivers, ponds, and rocky outcroppings. The wooden bridges are one of a kind and the course can play as hard as anywhere in the NY area. Great membership too, with a stately clubhouse that formerly was a robber baron’s mansion. After a weak opener, it’s all fireworks until the 18th hole, which plays as one of the toughest finishers in the region. The 16th hole is the picture you post to social but the punchbowl 15th is even more memorable. Full of great template holes and hole to possibly the best logo in golf. Gets overshadowed by Winged Foot but it’s every bit as good.
Freaking awesome. The land is A++. Greens super cool (#14 is absolutely wild). If you like templates (I do) you'll find some great ones here. #16 gets all the love as the photogenic Short but the Punchbowl 15th is the best hole on the golf course.
Some of the best par 3s in NYC area. Mix of memorable and meh par-4s. Plenty of elevation change between holes.
Incredible experience, world class club, massive property, interesting land movement and well worthy T100 status. Routing and greens are fantastic. Amazing set of par 3s. Maybe the best as a set. My favored hole is No. 3 par 3 Eden. What a green site.
CB Macdonald masterpiece. One of the best pro shops I’ve ever come across. The par 3s are maybe the best in golf. A Gil Hanse restoration has put Sleepy inside the top 100 in the US
Being lucky enough to play the Upper Course at Sleepy Hollow during the club championship was an unforgettable experience as the course was in perfect condition, and getting back-to-back sunsets over the Hudson made the entire setting feel surreal. The layout is an absolute blast to play, with so much variety throughout the round and a mix of challenging and fun holes that keep you dialed in the whole round and really any shot you are hitting into the green can go horribly wrong very quick if you aren’t careful. The bunkering around the greens is unlike anything I’ve seen before on a golf course. They are VERY deep, thick rough lined, and extremely demanding. If you end up in one, it takes a really good shot just to get it on the green. The greens were very fast and pure and if you left yourself above the hole, all I have to say is good luck🤣. The fairways and greens were firm, and the overall flow and design of the course made for one of the most enjoyable and memorable rounds I’ve ever had. Sleepy Hollow lives up to the hype and is without question one of the most special tracks I’ve played and the pictures definitely do that some justice.
Public courses closest to Upper at Sleepy Hollow Country Club.
Most visitors arrive via Westchester County Airport, a discreet executive hub just twenty minutes south, though many fly into New York's major gateways and drive the scenic hour north along the Hudson River's eastern shore. The approach to Sleepy Hollow Country Club traces the storied Route 9 through Tarrytown and into Scarborough, where the road narrows and the landscape softens into wooded estates and glimpses of the river below. The final turn onto Sleepy Hollow Road feels like slipping through a seam in time - dense hardwoods close overhead, and the clubhouse emerges quietly atop its bluff, a gracious sentinel overlooking one of the most hallowed stretches of American golf.
FAQ
Ratings, design, and course details pulled from Course Vaults.
Upper at Sleepy Hollow Country Club has a Course Vaults score of 9.2 out of 10 based on 130 explicit golfer ratings.
Upper was designed by Charles Macdonald and Seth Raynor.
Upper at Sleepy Hollow Country Club is listed as private on Course Vaults; guest access is typically restricted.
Par at Upper is 70.
Upper plays 6,902 yards from the back tees on Course Vaults.
The slope rating at Upper is 137.
