Sleepy Hollow Country Club in Scarborough, NY is a private, invitation-only club known for its historic estate, top-ranked golf courses, and extensive recreational amenities.
If you're considering joining or visiting, the short answer is yes—if you're looking for a well-rounded club experience rooted in tradition, sport, and community, it’s worth serious consideration.
Keep reading for a deeper look at what makes this club unique and how to get involved.
A Glimpse into the Legacy: History, Architecture & Modernization
From its Gilded Age roots to its thoughtfully modernized amenities, Sleepy Hollow Country Club blends timeless grandeur with quiet updates that support a more contemporary lifestyle.
Understanding where it started and how it’s evolved gives you a clearer picture of what the club offers today—and why that legacy still matters.
The Estate That Started It All
Sleepy Hollow Country Club is built on what was once “Woodlea,” the 140-room Vanderbilt mansion completed between 1892 and 1895.
Designed by the iconic architectural firm McKim, Mead & White, the estate was a towering example of Italian Renaissance Revival architecture, created during a time when opulence was part of everyday living for America’s wealthiest families.
It sits on 338 acres of historic land in the Scarborough Historic District, a designation that reflects both the cultural and architectural significance of the property.
What makes this history more than just decorative is how much of it remains visible and functional today.
The clubhouse itself is still centered in the original mansion, and you’ll see it the moment you arrive—from the soaring marble interiors to the finely detailed coffered ceilings.
While the Italian garden that once sat on the property has been replaced, the overall atmosphere hasn’t lost its formal beauty.
In fact, the club’s layout and landscaping continue to echo its historic roots.
Functionality Meets Heritage
Despite its historic standing, Sleepy Hollow has never been one to rely solely on tradition.
Over the years, careful renovations have preserved the estate’s character while making it work for a modern membership.
- The original mansion now houses three formal dining rooms that, together, can serve up to 400 guests—ideal for weddings, fundraisers, or large club events.
- A complete restoration of the pool complex brought in upgraded locker facilities, shaded lounge areas, and more family-friendly features without disrupting the scenic environment.
- New tennis pro shop and modernized locker rooms help the club meet current-day expectations, particularly for members with active lifestyles.
- Snack and bar areas were also refreshed, making them more welcoming for casual social time after sports or events.
Perhaps one of the most practical updates came in 2014, when the club installed solar panels—an eco-conscious decision that adds sustainability without compromising the look or feel of the estate.
These updates quietly reinforce a core principle that seems to guide the club’s evolution: improve what’s needed, protect what’s special.
The result is a space that continues to feel like a private escape, grounded in history but ready for the pace of today.
Whether you’re walking into a formal dinner or just spending a day by the pool, that sense of legacy is something you’ll notice—not just in how it looks, but in how it works.
Championship-Level Golf: Courses, Practice Facilities & Accolades
If you're serious about golf—or even just curious to explore a course with real architectural pedigree—Sleepy Hollow delivers in a way few clubs can match.
Its layout isn’t just scenic or challenging; it’s a living archive of golf course design, updated over time by some of the sport’s most respected names.
The 18-Hole “Upper” Course: A Timeline of Excellence
The crown jewel of Sleepy Hollow’s golf offerings is its 18-hole “Upper” course, which stretches 6,880 yards from the championship tees and plays to a par of 70.
It carries a course rating of roughly 73.8 and a slope of around 135—making it a strong test for low handicappers but still playable for mid-range golfers with the right strategy.
Originally designed in 1913 by Charles Blair Macdonald and Seth Raynor, two icons of the Golden Age of golf course architecture, the course has undergone several thoughtful revisions.
A.W. Tillinghast made notable changes in 1935, followed by Rees Jones in 1992 and Gil Hanse in 2008.
Each redesign brought new life to the layout while respecting its roots, ensuring a continuous thread of strategic variety and visual drama.
The course is frequently praised for:
- Its elevated tee boxes and riverfront holes that showcase stunning views of the Hudson River
- A wide range of shot angles and fairway widths that favor creativity over power alone
- Architectural throwbacks like squared-off greens and subtle contouring that reward local knowledge
These elements help explain why Sleepy Hollow consistently ranks among America’s top 100 golf courses.
For many, it’s not just about playing 18 holes—it’s about experiencing golf as a blend of sport and art.
A Faster Round: The 9-Hole Executive Course
For members who want a quicker round, a warm-up, or a more relaxed option for beginners or families, the club also offers a 9-hole Executive course laid out in 1914.
At approximately 1,979 yards and a par of 31, this course offers a refreshing pace without skimping on thoughtful hole design.
It’s especially useful for:
- Juniors and newer players building confidence
- Members with limited time for a full 18-hole round
- Short-game practice in a real-course setting
Despite its smaller footprint, the Executive course maintains a high standard of maintenance and enjoys the same scenic qualities as the Upper course.
Practice Facilities That Match the Courses
Supporting both courses is a full suite of practice options, including a well-maintained driving range, putting greens, and a fully staffed pro shop.
Members can rent clubs, book private lessons, and use electric carts, making it easy to get on the course regardless of skill level or equipment availability.
The attention to detail in the practice areas reflects the club’s broader approach to golf—designed for long-term growth, regular play, and a welcoming experience for all skill levels.
Whether you’re preparing for tournament play or just trying to improve your short game, the facilities are ready for both.
More Than Just Golf: Recreational & Lifestyle Amenities
While golf may be the headline attraction at Sleepy Hollow Country Club, the lifestyle it offers extends well beyond the course.
For members looking for variety in how they spend their time—or simply seeking a well-rounded club experience—there’s a deep bench of activities, programs, and services designed to meet a wide range of interests.
Racquet Sports for All Seasons
Tennis is a year-round pursuit here.
The club features 10 Har-Tru clay courts, which are known for being gentler on joints and preferred by many experienced players.
These outdoor courts are ideal during spring and summer, with clinics, lessons, and competitive ladders typically running throughout the warmer months.
When the weather cools, racquet play doesn’t stop.
Members can switch to four heated platform tennis courts—popular for their fast pace and cold-weather friendliness.
Additionally, four squash courts are available indoors, offering a great option for high-intensity workouts or off-season training.
This spread of racquet sport options allows members to stay active and social no matter the time of year.
Pool & Fitness Amenities
The swimming complex isn’t just for lounging—it’s fully equipped with locker facilities and designed for families, lap swimmers, and event hosting alike.
The setting maintains the club’s classic charm while catering to the practical needs of daily use.
Whether you’re enjoying a summer afternoon with your kids or joining a morning swim group, the pool area is versatile and well-maintained.
The fitness center adds another layer of convenience.
You can use it for casual workouts or take advantage of personal training options.
It’s not a massive gym, but it’s enough to cover the basics—cardio equipment, weights, and functional training space—especially for members who want to keep active without leaving the club grounds.
Equestrian Offerings with Serious Capacity
One of Sleepy Hollow’s standout features is its full-service riding academy, a rare perk among country clubs.
The equestrian program includes an indoor arena for year-round lessons and riding, outdoor paddocks, and boarding for approximately 45 horses.
Riders of all ages and levels can take part, whether they’re looking for recreational trail rides or more formal instruction.
For families with horse enthusiasts or those considering a new hobby, this program adds unique value and supports ongoing involvement in the sport without needing a separate facility.
Shooting Sports On-Site
For members interested in marksmanship or looking to try something different, the club also provides skeet and trap shooting facilities.
These aren’t just seasonal pop-ups—they’re permanent installations, offering a structured environment for beginners and enthusiasts alike.
While not the club’s most prominent activity, it’s a welcome bonus for those who enjoy outdoor sport beyond the usual mix.
Guest Rooms for Convenience and Events
The club includes 18 on-site guest rooms, available for members or event guests.
These rooms are ideal for hosting visiting friends or accommodating overnight guests during weddings, tournaments, or holiday weekends.
Having lodging on-site adds a layer of convenience and helps support the club’s broader role as a social and event destination.
Membership Demystified: Options, Costs & What to Expect
If you're thinking about becoming a member at Sleepy Hollow Country Club, understanding how the membership structure works can help you figure out if it aligns with your lifestyle, goals, and budget.
The process is selective and community-oriented, but the range of membership types offers flexibility for different needs and stages of life.
Membership Structure and Types
Sleepy Hollow currently has a base of around 570 members, supported by a dedicated staff of about 60 year-round employees.
During peak seasons, that number grows to roughly 200, ensuring the club maintains high service standards across all its amenities and activities.
Membership is by invitation only, which means you’ll need to be referred by a current member or have a close connection to the club in some way.
This process isn’t just about exclusivity—it’s designed to maintain a tight-knit, engaged community that values participation and mutual respect.
To accommodate varying lifestyles, the club offers several membership categories. These include:
- Family and Single memberships, ideal for individuals or households looking to make the most of the club’s broad amenities
- Young Professional and Junior memberships, which appeal to those early in their careers or under a certain age threshold
- Golf & Dining or Weekday Golf memberships, designed for members with more targeted interests or time availability
- Young Social and Social memberships, focused more on events, dining, and casual access to facilities without full golf privileges
- Extended Area memberships, which may apply to those living outside a specific radius but still wishing to participate in club life seasonally
Each category has different access levels, so it’s worth discussing your priorities—whether it’s golf, family use, or social engagement—before choosing a track.
Costs and Financial Commitments
The financial side of membership is straightforward but does require a clear understanding of both initial and ongoing costs.
- Initiation fees are generally set at $10,000, though the Young Social membership is more accessible, starting at $2,500.
- Monthly dues vary by category, ranging from around $108 to $400, depending on your membership type and level of access.
- In addition to these recurring dues, members should also plan for deposits, range fees, and a minimum food and beverage spend, which helps support the club’s dining and event offerings.
These costs reflect the scope and quality of the club’s amenities, as well as the staffing and upkeep required to maintain them at a high standard.
What to Expect as a Member
Joining Sleepy Hollow means more than gaining access to facilities—it’s about entering a community with a shared interest in recreation, social connection, and club culture.
The atmosphere strikes a balance between tradition and approachability.
Whether you're a competitive golfer, an event regular, or someone who prefers quieter enjoyment of the grounds, there’s room to find your niche.
Club life includes everything from tournaments and holiday parties to casual gatherings and interest-based groups.
It’s active without being overwhelming, and the emphasis is on shared experience, not status.
The invitation-only aspect fosters a sense of mutual familiarity, which is part of why many members stay long-term and become deeply involved in club life.
If you’re considering applying, it’s a good idea to start by identifying the membership category that fits your situation.
Then, reach out to a current member or club staff to learn about availability, timelines, and referral expectations.
The application process is generally smooth for those who are serious, well-prepared, and aligned with the club’s culture.
Culture, Events & Media Appearances: Club Life in Action
Sleepy Hollow Country Club is more than just a venue for sports and relaxation—it’s a social hub with a strong sense of community, a rich event calendar, and a presence that extends well beyond its gates.
Whether you're interested in competitive play, casual gatherings, or cultural cachet, the club offers a lifestyle that balances tradition with relevance.
A Culture That Blends Tradition and Camaraderie
The social culture at Sleepy Hollow is built on participation and connection.
Competitive and casual golf are certainly focal points, but they’re just part of a broader club identity that values member relationships, shared experiences, and year-round engagement.
Club life here feels active but not overwhelming.
It’s common to see the same members at golf tournaments in the summer, paddle matches in the winter, and evening dinners or holiday parties throughout the year.
The atmosphere is welcoming but remains centered around longstanding values—polish, courtesy, and mutual respect.
For prospective members, it’s worth knowing that the culture is inclusive within its community but does lean toward participation.
Members who attend events, join teams, or host guests tend to get the most out of what the club has to offer.
Events That Bring the Club Together
Sleepy Hollow hosts a robust calendar of events throughout the year, including:
- Seasonal tournaments and championships across golf, tennis, and paddle
- Club-wide social events like themed dinners, member mixers, and holiday celebrations
- Private functions, where members can host weddings, corporate retreats, or family gatherings with full event support
These events serve both social and competitive purposes, giving members multiple ways to engage regardless of their interests.
The formal dining spaces—capable of hosting up to 400 guests—often serve as the backdrop for these larger gatherings, while more intimate events take place in lounges or outdoor settings across the estate.
A History of High-Profile Tournaments
Sleepy Hollow also has a tournament pedigree that reinforces its stature in the golf world.
It hosted the NYNEX Commemorative from 1986 to 1993, a PGA Senior Tour event that brought top names in golf to the club. In 2002, it welcomed the U.S. Women’s Amateur, adding to its national relevance in competitive play.
These events weren’t just footnotes—they’ve contributed to the course’s evolution and added to the club’s broader reputation within elite golf circles.
A Popular Filming Destination
Beyond sports and socials, Sleepy Hollow has also become something of a star in its own right.
Its iconic mansion and scenic grounds have appeared in numerous TV shows and films, including:
- Madam Secretary
- Gotham
- Daredevil
- The Good Wife
- Quantico
- The Bounty Hunter
- The Greatest Showman
- Beyoncé’s Best Thing I Never Had music video
Its appeal to producers is no mystery—the estate offers timeless elegance, sweeping Hudson River views, and interiors that work equally well for period dramas and upscale modern shoots.
For members, this means more than bragging rights.
It speaks to the quality and uniqueness of the club’s setting, and to the care taken to preserve its visual and historical integrity.
Getting Involved: Visiting, Booking, and Membership Inquiries
If you’re interested in exploring Sleepy Hollow Country Club as a guest, event host, or potential member, there are a few specific steps to follow.
Access is selective but not opaque—and with the right information, the process is straightforward and approachable.
Visiting the Club: How to Get In
Because Sleepy Hollow is a private, invitation-only club, general public access isn’t available.
However, there are a few pathways to visit the grounds or tour the facilities:
- By invitation: The most common way to visit is through an invitation from a current member, whether for golf, a social event, or an informal tour.
- Through open days or special events: On rare occasions, the club may host open houses or prospective member events. These are usually invite-only or promoted internally through current members.
- Member referral for tour purposes: If you’re seriously considering membership and have a personal or professional connection to an existing member, they may help arrange a formal visit.
Keep in mind that all visits are subject to availability and club discretion.
If you’re hoping to explore membership, it’s best to coordinate directly with the membership office or through someone in the club network.
Golf Booking and Guest Play
Tee times at Sleepy Hollow are not available for general booking.
All rounds must be arranged via:
- A current member host, who can invite guests to play
- Direct coordination with golf staff, typically for member-sponsored guests or events
Practice facilities and lessons also fall under the same access structure.
If you’re invited to play, you can expect high-quality rental clubs and electric carts available through the pro shop.
For out-of-town guests or tournament weekends, planning ahead is recommended to secure tee times and any additional accommodations, such as access to the guest rooms or locker facilities.
Hosting Events on the Grounds
Sleepy Hollow’s historic mansion and expansive grounds make it a popular venue for weddings, corporate retreats, and club-hosted events.
The club can accommodate up to 400 guests across its three formal dining rooms, and 18 on-site guest rooms are available for overnight stays, creating a full-service event experience.
Event hosts typically need to be members or work with a sponsoring member, though exceptions may be made depending on the occasion and season.
For weddings and major functions, advanced booking—sometimes up to a year or more in advance—is common.
The club provides full event support, including catering, staff coordination, and setup, all tailored to fit the occasion and maintain the club’s elegant presentation.
Filming and Media Requests
Given its track record of high-profile media appearances, Sleepy Hollow remains open to select filming and commercial projects.
However, all media rental inquiries must go through the club’s media relations or administrative office. Proposals are reviewed for scheduling, impact on members, and brand alignment.
Filming on-site is possible but tightly controlled, so early outreach and detailed proposals are essential if you're planning a shoot.
How to Join: Step-by-Step
If you’re ready to explore membership, here’s what to expect:
- Identify the right membership category for your lifestyle and interests—whether that’s Family, Golf & Dining, Young Professional, Social, or another tier.
- Secure a referral or introduction from a current member or club staff.
- Submit a formal application, which includes basic information, references, and a summary of your interest in joining.
- Prepare for initiation and ongoing costs, including initiation fees (typically $10,000 or $2,500 for Young Social), monthly dues ($108–$400), deposits, and minimum food spending.
You may also be invited for an informal interview or club visit as part of the vetting process.
Smart Considerations Before You Apply
Before applying, take some time to evaluate whether the club fits your lifestyle and long-term goals. Consider the following:
- How often you’ll use the facilities—especially golf, dining, and racquet sports
- The social culture and event calendar—and whether you’d want to participate
- Your budget, including both upfront and recurring expenses
- Location and access, especially if you live outside the immediate area
Joining Sleepy Hollow is as much about joining a community as it is accessing facilities.
The more clearly you understand your priorities, the better the fit—and the more value you’ll get from your membership.
Whether you’re hoping to play on one of the nation’s most celebrated golf courses, host an unforgettable event, or simply become part of a private, historic club, there are clear paths to getting involved—so long as you’re ready to take that first step.
Conclusion
Sleepy Hollow Country Club offers a rare combination of historic charm, elite-level golf, and a broad range of lifestyle amenities.
Whether you're considering membership, hosting an event, or planning a visit, it’s a setting designed for both tradition and thoughtful recreation.
If it aligns with your interests and values, taking the next step could be well worth it.
