Navigating New York’s historic golf trail with a day-by-day itinerary
Latest updated: 16th October 2025
Reading time: 5 minutes
Introduction to New York’s historic golf trail
New York State offers more than just iconic skylines and bustling city life; it is also home to some of the most storied and celebrated golf courses in America. From the rolling dunes of Long Island to the secluded charm of Fishers Island, the state’s golf trail is a journey through time, culture, and natural beauty. This article will guide you through a carefully crafted day-by-day itinerary, combining legendary courses like Shinnecock Hills, Winged Foot, and Fishers Island with rich storytelling, local insights, dining recommendations, and scenic experiences. Whether you’re a dedicated golfer or a lover of history and landscapes, this trail promises an unforgettable adventure.
Day 1: Shinnecock Hills – The birthplace of American golf excellence
Your journey begins on Long Island at Shinnecock Hills Golf Club, one of the oldest golf clubs in the United States, established in 1891. Known for its wind-swept links-style layout, Shinnecock is a revered test of skill, having hosted multiple U.S. Opens. But beyond the challenge lies an intriguing history: the land was originally inhabited by the Shinnecock Nation, and the course’s design honors the natural topography, preserving the native landscape unlike many other courses altered heavily through construction.
Practical tip: Book your tee time well in advance; public access is limited, but the club occasionally opens for tournaments and select outings. Consider timing your visit during the early morning hours to enjoy the serene atmosphere before crowds arrive.
After your round, explore the nearby village of Southampton, where you can dine at The American Hotel, a historic inn featuring farm-to-table cuisine, perfect to unwind and reflect on the day’s play.
Day 2: Winged Foot – The ultimate championship course
Next, head to Winged Foot Golf Club in Mamaroneck, renowned for its two championship courses: the East and the West. The East Course, famous for testing legends during the U.S. Open, offers undulating greens and strategic bunkering designed by A.W. Tillinghast. Its challenging fairways have witnessed some of golf’s most dramatic moments, including the legendary battles of the 1929 and 2006 U.S. Opens.
Course insight: Winged Foot’s West Course is equally worthy of exploration, especially for those interested in architecture and history. It’s a hidden gem that offers a contrasting style, a bit less brutal but still a formidable test.
Local culture: After your round, immerse yourself in the local culture by visiting Rye’s waterfront area nearby or enjoying craft cocktails and seafood at The Capital Grille in White Plains, where the ambience complements the upscale golfing experience.
Day 3: Fishers Island – The hidden island retreat
For a unique and secluded golf experience, take the ferry to Fishers Island Club. This private course, designed by Seth Raynor, blends classic design with spectacular ocean views, offering an atmosphere that few courses can match. Its isolated location has preserved both natural beauty and a sense of exclusivity.
Hidden story: Fishers Island served as a coastal defense hub during World War II, with some remnants still visible around the island. After your game, explore the walking paths near Fort H. G. Wright for a glimpse into the island’s military history.
Dining and scenery: End your day with fresh seafood at The Pequot, known for its cozy setting and regional specialties that celebrate Long Island’s rich coastal cuisine.
Additional tips for an enriching golf trail experience
- Transportation: Renting a car is essential for seamlessly navigating between courses. Plan your routes ahead, especially ferry schedules for Fishers Island.
- Accommodation: Towns like Southampton and Rye offer charming inns and boutique hotels that combine comfort with proximity to these historic clubs.
- Gear and preparation: Weather on the trail varies seasonally; bring layered clothing and prepare for coastal winds especially on Shinnecock and Fishers Island.
Frequently asked questions
Can non-members play at these historic courses?
While many prestigious clubs like Shinnecock Hills and Fishers Island Club are private, some offer limited public access through tournaments, reciprocal memberships, or special arranged rounds. Winged Foot, being highly exclusive, is even more restrictive. Planning ahead and checking club websites or contacting concierge services can help identify opportunities to play.
What’s the best time of year to visit New York’s golf trail?
Late spring through early fall (May to October) provides the best weather with mild temperatures and vibrant landscapes. September offers particularly beautiful fall foliage, adding to the scenic value of each course.
Are there guided tours focusing on the history and architecture of the courses?
While formal tours are rare, some clubs and local golf historians offer private or group tours during off-peak seasons or around major tournaments. Additionally, golf enthusiasts often provide informal guided experiences through golf travel communities and clubs.
What should I know about dining options along the trail?
The trail is surrounded by rich culinary scenes reflecting local flavors. From upscale dining in Southampton to cozy seafood shacks on Fishers Island, you’ll find everything from farm-to-table meals to classic Long Island specialties like lobster rolls and clam chowder. Booking reservations in advance is advisable during peak seasons.
Conclusion
Exploring New York’s historic golf trail is more than just a sporting adventure; it’s a deep dive into American golf heritage, culture, and the breathtaking landscapes that shaped the game. From the windswept links of Shinnecock Hills to the championship rigor of Winged Foot and the secluded charm of Fishers Island, every day offers new stories, challenges, and delights. By following this day-by-day itinerary and immersing yourself in the local culture and history, you’ll experience a golfing journey unlike any other.
Whether you’re a seasoned golfer, a history buff, or a traveler seeking unique experiences, New York’s historic golf trail promises memories that will last a lifetime.