Sleepy Hollow Country Club is a historic country club in Scarborough-on-Hudson in Briarcliff Manor, New York. The club was founded in 1911, and its clubhouse was known as Woodlea, a 140-room Vanderbilt mansion owned by Colonel Elliott Fitch Shepard and his wife Margaret Louisa Vanderbilt Shepard. It was built in 1892–95 at a cost of $2 million and was designed by the architectural firm McKim, Mead & White; the estate became a contributing property to the Scarborough Historic District in 1984.

Briarcliff Manor is a suburban village in Westchester County, New York, 30 miles (50 km) north of New York City. It is on 5.9 square miles (15 km2) of land on the east bank of the Hudson River, geographically shared by the towns of Mount Pleasant and Ossining. Briarcliff Manor includes the communities of Scarborough and Chilmark, and is served by the Scarborough station of the Metro-North Railroad's Hudson Line. A section of the village, including buildings and homes covering 376 acres (152 ha), is part of the Scarborough Historic District and was listed on the National Register of Historic Places in 1984. The village motto is "A village between two rivers", reflecting Briarcliff Manor's location between the Hudson and Pocantico Rivers. Although the Pocantico is the primary boundary between Mount Pleasant and Ossining, since its incorporation the village has spread into Mount Pleasant.