Course info
Score
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Course Report
Sleepy Hollow Country Club sits on land once home to a 140-room Vanderbilt mansion, which is now the clubhouse with 18 hotel rooms. The course features "haunted" timber bridges built in 1820s style, referencing The Legend of Sleepy Hollow, where the Headless Horseman couldn’t cross a bridge.
About
Sleepy Hollow Country Club's Upper Course, designed by Charles B. Macdonald and expanded by A.W. Tillinghast, is a celebrated parkland layout perched above the Hudson River, notable for its historic architecture and meticulously restored classic holes by Gil Hanse. The private club regularly features among America's top 100 courses, admired for strategy, scenery, and Golden Age pedigree.
Caddie Tip
Play for smart angles into the classic Macdonald greens—many reward approach shots from the correct side of the fairway. Be ready for fast, contoured putting surfaces and variable winds. Study the false fronts and strategic bunkering, and don’t underestimate the challenge if approaching from above the hole or long rough.
The Main Challenge
The steep greens and creative bunkering demand precise iron play and short-game control. Subtle doglegs, elevation changes, and crosswinds from the nearby river add difficulty. A strong finish—especially holes 15 through 18—tests even experienced players, with hazards and greens that demand full concentration.
The Good
Golfers are drawn to Sleepy Hollow Upper for its Golden Age design pedigree, gorgeous river views, and sense of history. The recent restoration by Gil Hanse elevated the course’s original strategic intent and visual drama, leading to enhanced acclaim and replay value that satisfies both architecture students and social golfers.
The Not So Good
Some visitors feel the course’s exclusivity, strict traditions, and member-focused facilities can make it intimidating for guests. A few holes have blind shots or slopes that can frustrate first-timers, and club access is limited due to private policies.
Signature Hole:
#
16
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Hole 16, a par 3, is widely considered the iconic hole at Sleepy Hollow Upper. The tee shot plays steeply downhill, with panoramic Hudson River views as a dramatic backdrop. The green is defended by bunkers and severe slopes, making club selection vital. This hole’s beauty and challenge have made it a standout in American golf course architecture.
Clubhouse
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The Woodlea mansion clubhouse features fine dining, casual lounges, locker rooms, and expansive patios with river views. Other amenities include a pro shop, pool complex, tennis and squash courts, fitness center, riding stables, and overnight guest rooms for members and their guests.
Practice Facilities
The club offers a full practice range with grass tees, a short game area including sand bunkers, and multiple putting greens. Instruction is available from the professional staff, and the environment emphasizes quiet, uncrowded preparation typical of private clubs.
Dress Code:
Prestigious
No dress code enforced. All attire is permitted.
Collared shirts not required. Clean, athletic or golf-appropriate casual wear is acceptable.
Collared shirts required. No denim, gym wear, or overly casual clothing.
Collared shirts must be tucked in; no cargo or athletic shorts. No hats indoors.
Elite club standards; jackets required indoors, no changing shoes in the parking lot, and specific attire rules based on the area of the facility.
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