Sleepy Hollow is a storied enclave where championship golf meets Gilded Age elegance along the Hudson River. This classic, early 20th-century parkland design, sculpted from rolling Westchester County hills, demands strategic play and precise approaches to undulating greens. Originally crafted by the master hand of C.B. Macdonald, with later enhancements by A.W. Tillinghast and Gil Hanse, Sleepy Hollow challenges golfers with a variety of demanding doglegs and dramatic elevation changes. Although it hasn't hosted major championships, the club maintains a discreet reputation among those who appreciate the finer aspects of the game, and the historic setting. Sleepy Hollow’s membership, drawn from the New York City area's business and social elite, carries on traditions that predate the club's formal establishment. Legend has it that the land's previous owner, William Rockefeller, would invite friends for informal rounds, setting the stage for what would become a bastion of northeastern golf. And keep an eye out for the resident hawks, who are known to occasionally snatch a golf ball right off the green, adding an unexpected hazard to an already challenging round.