Golf

Item Description

Enjoy stunning views of the Hudson River, traverse hand-made wooden bridges, and test your skills at one of America’s top golf courses. Sleepy Hollow Country Club is ranked #59 in Golf Digest's Top 100 courses in the U.S. and hosted the 2023 U.S. Mid-Amateur tournament. Noted golf architect Gil Hanse executed an award-winning renovation and restoration of golden age architect C.B. Macdonald and Seth Raynor’s design, elevating Sleepy Hollow as one of the best course renovations according to golf.com and Golf Digest. Sleepy Hollow Country Club is located in Scarborough, NY just north of New York City.

Offering a threesome to golf with member-host Garrett Schires. Caddies, food and beverage included!

Date and time must be mutually agreed upon within a year of purchase (March 2025). 

*Overnight clubhouse accommodations can be made for out of town guests for a small fee.*

The 338 acres of "Washington Irving" hills and woodlands that make up the Sleepy Hollow Country Club were once known as Woodlea, the country estate of Colonel Eliot F. Shepard and his wife Margaret Vanderbilt. Margaret was the daughter of William H. Vanderbilt and a granddaughter of railroad magnate Cornelius Vanderbilt. In 1893 Colonel Shepard engaged one of America's most noted architects, Stanford White, to design the manor house, which today is the main clubhouse. The entire estate was purchased in 1910 by Mr. William Rockefeller and Mr. Frank A. Vanderlip who, in May 1911, organized Sleepy Hollow Country Club with other prominent New Yorkers including John Astor, Edward Berwind, and Averell Harriman.

To build their golf course, the founders turned to Charles Blair Macdonald, the preeminent golf course architect of the time. Macdonald and his apprentice, Seth Raynor, built the course during the summer of 1911 and it opened for play in the spring of 1913. The Course was immediately recognized as one of the finest in the country. At the end of the 1920's, A.W. Tillinghast, another legendary golf architect, expanded the facilities to 27 holes. The recent renovation by Gil Hanse and George Bahto united the course architecture under Macdonald’s template hole designs and restored the original character to all twenty-seven holes.

Item Special Note

Golf must be played within a year of purchase (April 2025). Credit card fees may apply.