In 1911 when Sleepy Hollow opened, golf course design in America was still in its early stages. Neither Pine Valley nor Alister Mackenzie’s work existed. Oakmont and Pinehurst No. 2 had yet to evolve into the masterpieces that we now know. Northeast courses like Myopia Hunt, Ewkanok, The Country Club and C.B. Macdonald’s newly opened National Golf Links of America were the standard bearers.
Built for a who’s-who group of businessmen headed by William Rockefeller, Macdonald’s design at Sleepy Hollow brought time proven design concepts from the Scottish links that he cherished to an inland setting one hour northeast of New York City. Central bunkering, a Redan (in this case, a reverse one) and a punchbowl green are examples of traditional features to which Macdonald was keen to expose to the American golfer, and he did so here.
Neither Macdonald nor Rockefeller were known for their shrinking egos and the two had a falling out before the course opened. Nonetheless, Sleepy Hollow proved highly successful and by the late 1920s, A.W. Tillinghast was brought in to increase the number of holes to twenty-seven. In so doing, Tillinghast created the first, eighth through twelfth and eighteenth holes and then knitted them into Macdonald’s course.