Well, I’m having trouble knowing where to begin with Sleepy Hollow. Just as much trouble, in fact, as knowing where to end. I could save us both some time by summing it up in a single line: Sleepy Hollow is the most quintessential American golf course. There. Done. No elaboration required. Move on with your life.

But maybe I need to sleep on that notion. It is October after all, and my brain may be swimming in a pumpkin-spiced fog. The leaves on the deciduous trees are in full retreat, our tee time was delayed by autumn frost, and here we are, playing golf on what feels like Halloween’s home turf. Maybe I’m just under the influence of a holiday that I have always tied closely to this country.

It could be the way the course looks over the Hudson River, that wide tidal estuary that once carried the economic lifeblood of a nation inland, linking canals and tributaries that pushed America’s industrial heart westward. It pulled the centre of gravity away from the colonial ports of Boston and Philadelphia and into a new era.

Or maybe it is the Gilded Age history baked into the property. This land once belonged to Colonel Shepard and Margaret Vanderbilt, who envisioned a manor of unapologetic opulence. Then came the titans: Rockefeller, Vanderbilt, Astor, Vanderlip, Harriman, Macy, Choate and Colgate. Their vision was to reshape and reprogram the land with golf, and for that they summoned Charles Blair Macdonald, the godfather of American golf architecture. Macdonald’s fingerprints are all over the nation’s early great courses, his designs setting a blueprint for what American golf would become.

The focal lone tree located central to the course.

Not long after, Albert Warren Tillinghast added his own eccentric brilliance. He was a man who designed as though possessed, free, unfiltered and untethered by modern constraint. The early twentieth century was golf architecture’s golden age, and Sleepy Hollow stands as a living, breathing artifact of that time.

Standing on the property, looking across the broad, sweeping landscape, my tiny brain struggled to make sense of it all. The place is enormous. The beauty, almost theatrical. The course matches nature’s energy with grand, deliberate gestures. At times it drapes itself elegantly over the terrain, flowing down hollows and across rocky shoulders. At others, it thrusts greens high into the air, connected by ornate footbridges that seem as if they have always belonged.

That is what I love about the Macdonald, Raynor and Banks style. They did not simply blend their work into the environment. They formalised it. They celebrated it. They took the drama of nature and set it to a template, like a jazz musician riffing on a familiar tune. It is not subtle. It does not need to be. The course wants to be part of the story, like a mascot on the sidelines, waving its arms and urging the crowd to join in.

Sleepy Hollow is Halloween, Gilded Age grandeur and American golf mythology all rolled into one. It is a love letter written in stone, soil and template greens. Like any great American story, it is part history, part theatre, part self-mythologising, and entirely unforgettable.

Walking off the 18th green and you don’t need to be a golfing savant to know that you’ve completed a special round of golf. A round of golf that perfectly encapsulates golf in America.

Happy Golfing