Fenway’s stature as one of the pre-eminent golf clubs in Westchester results from the time tested greatness of its golf course and the rich history of its professionals. The course was designed in 1924 by A.W. Tillinghast, one of America’s greatest architects. Often dubbed "Little Winged Foot", Fenway’s severely sloping greens, deep traps and deceptively difficult landing areas, have proven time and time again that this golf course need be compared to no other and stands on its own as a premier test of golf excellence.
Whether as host of the 1938 "Westchester 108" (boasting the then highest purse on the PGA tour), the Westchester Open, the Westchester PGA or numerous US Open qualifiers, no professional or amateur has yet to bring Fenway to its knees. As recently as the 1987 Metropolitan Open, Rick Vershure lapped the field at 8-over par for 54 holes. Golfing greats Sam Snead and Byron Nelson have lauded Fenway greens and Tommy Armour referred to the course as "one of America’s best".