Caddie Climber|TCR has it much higher than national consensus.
Established
1928
Architect
Charles H. Banks (original/redesign, 1928); Donald Ross (initial routing, mid-1920s); Tripp Davis & Associates & Nicklaus Design (renovation 2022–2025)
Access
Private
Par
Par 71
Length
4,915 – 6,724 yds
The verdict
A Golden Age Thrill Ride
Whippoorwill Club is a dramatic Charles Banks classic where template holes, steep terrain, and bold greens blend for a truly strategic round. Recent renovations have reinvigorated playability and restored its historic flair, making it a must for architecture buffs and a centerpiece of Westchester golf lore.
Course DNA
Difficulty
84
Scenery
82
Conditioning
87
Shot Variety
90
Walkability
68
Green Complexity
92
Wow Factor
86
Design Quality
94
Don't miss
When you reach the pond at No. 7, remember there may be an entire steam shovel buried beneath it — club legend says one sank out of sight during construction and was never recovered.
At a glance
Quick facts
Signature Template Holes
Biarritz (8th), Redan (11th), Short (4th)
Course Elevation
Sits atop one of Westchester’s highest points
Property Size
Spread across 170 scenic acres
Recent Renovation
Restoration 2022–2025 revived its Golden Age identity
Playing Surfaces
Larger, undulating greens and native grass restoration
Historic Clubhouse
Commanding views beside the iconic 18th
Routing Character
Distinctive east (open) and west (hilly) nines
Bunkering Style
Restored bold, steep-faced Banks bunkers
The design
The architecture
Whippoorwill Club is Golden Age drama in three acts: Ross's original vision, Banks’s strategic brilliance, and a recent revitalization bringing both into the 21st century. The course is a parade of template holes—Short, Biarritz, Redan—interwoven with bold landforms that create elevated tees, sloping fairways, and high-stakes approaches. The recent multi-year restoration has recaptured Banks’ sprawling greens, intricate bunkering, and classic playing angles, while native grasses and tree removal have emphasized the striking terrain. Every stretch, especially over Whippoorwill Road, feels like a test of shotmaking, course management, and nerve.
Charles H. Banks’s hand is everywhere: from the bold, square-edged bunkers to heroic carries over yawning valleys, this is template-driven architecture at its most exuberant.
Defining features
Restored template holes—Biarritz, Redan, Short—each playing true to their strategy
Dramatic elevation changes, especially on the west side
Large, undulating greens restored to Banks’ original intentions
Deep, steep-faced bunkers with revived sandy edges
Strategic teeing options and broadened fairways post-renovation
Removal of white pines and reintroduction of native grasses for original feel
Hole by hole
Signature holes
Hole 4
Short
PAR
3
YARDAGE
157 yds
A Banks ‘Short’ par 3 where a precise wedge is mandatory; the green is wide but flanked by steep bunkers, punishing the imprecise. The challenge is all in the distance and spin control.
Play it smart
Aim for the proper section of the broad but shallow green. Short is safe, but miss left or right and you’re facing a daunting up-and-down.
Where it bites
Steep-faced bunkers grab any shot not hit precisely—misjudge distance and par becomes elusive.
Course management
Shots to think about
Approach to Biarritz 8th with back pin
Be bold—carry it all the way to the rear tier, as short shots face an impossible two-putt from the swale.
Tee shot on hilly par-4 5th
Aim right and favor a draw; fairway pinches and rough lurk left.
Long iron to Redan 11th
Let the ball land front-right and ride the contour—direct attacks rarely hold.
Second shot on par-5 16th
Think position, not power. Play short of bunkers for a clear third and a chance at birdie.
Uphill approach to 18th green
Take an extra club for the elevation, but beware overshooting—short is better than long here.
Chipping from tight lies around expanded greens
Use the ground—Banks’ greens invite creative bump-and-run, not only aerial shots.
On the day
What to expect
Conditions
Firm, impeccably kept fairways and greens, with crisp restored bunkers and true putting surfaces.
Pace
Moderate traditional private-club pace; rounds are generally unhurried but steady.
Vibe
Serious yet welcoming private club, with a reverence for history and quiet, understated exclusivity.
Dress code
Standard private-club attire: collared shirt, tailored shorts or slacks, appropriate golf shoes.
Before you tee off
Your game plan
01
Practice Your Distance Control
The par 3s, especially Biarritz and Redan, demand exactness—know your long irons.
02
Be Ready for Uneven Lies
The hilly terrain regularly offers sidehill and downhill stances—train for variety.
03
Sharpen Your Short Game
Restored expansive greens and run-off areas mean you’ll face plenty of tricky chips.
04
Study Template Greens
Brush up on classic green shapes—Biarritz, Redan, and Short punish the unprepared.
The lore
How it came to be
1928
Charles H. Banks undertakes dramatic redesign and routing
2017
Returns to Golfweek’s Top 100 Classic Courses (No. 92)
Stories & legends
What makes it special
template-lore
The Biarritz and the Bird
The 8th hole is not just the club’s iconic template par 3—it’s named for the famous French design and is shadowed by the call of the Whippoorwill bird, said to echo over the hilltops at dusk. The blend of Banks’ architecture and nature’s own soundtrack makes for a unique Westchester memory.
routing-drama
Battle Across the Road
Players still talk about the moment the routing moves over Whippoorwill Road—here, Banks flexed his creativity, carving tough long par 4s through rocky, tree-lined corridors and creating holes that demand every shot in your arsenal. It’s the section where rounds can soar—or unravel.
modern-restoration
Return to Classic Roots
The Tripp Davis and Nicklaus Design renovations didn’t just touch up the greens—they revitalized the soul of Whippoorwill, restoring bunkers, opening green edges, and recapturing Banks’ original flair. Architecture critics and members alike say it’s brought the course roaring back to its rightful stature.
memorable-close
18th Hole Finish—Flag and All
The climb to the 18th is a fitting climax: from the undulating fairway, golfers play uphill to a green framed by a stately clubhouse and soaring flagpole, watched over by a wraparound gallery of history and tradition.
For the group chat
Fun facts
1
Named for the nightjar bird whose call echoes over the property’s hills
2
Famous for dramatic elevation and no parallel holes—each hole is carved into its own corridor
3
Signature flagpole on the 18th green is a local legend and finishing touch
4
Banks’ bunkers here are among the boldest and steepest of the Golden Age cohort
5
Template holes are not just historic—recent restoration made them truer to Banks’ original vision
Build the trip
Building a true Westchester classic golf itinerary
CourseAccessWhy it's on the listTrip
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Sleepy Hollow Country Club
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Wykagyl Country Club
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Elite old-line Westchester private—immaculate and storied
Mount Kisco Country Club
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Solid private club close by with classic New York golf
White Plains/Armonk for easy access to Whippoorwill and Westchester’s finest clubs and public options
Course DNA
If You Like Whippoorwill Club
Courses with the most similar DNA profile — matched by deviation shape across all eight playing characteristics.
Community Sentiment
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