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".

Fenway history has also been made rich by the quality of its professionals. All time greats and Hall of Famers Leo Diegal and "Wild Bill" Mehourne represented Fenway on tour in the 20’s and 30’s. Follwing them a young player from Port Chester, NY, named Herman Barron settled into the Head Pro position. Over the next four decades, Herman became a golfing legend both at Fenway and throughout the United States. A leading tour player, he captured the Western Open, Philadelphia Inquirer, Goodall Round Robin, World Championship along with scores of other tour and local events. Herman was a member of the 1947 Ryder Cup Team and is enshrined in the Westchester Hall of Fame.

Herman was succeeded by Jimmy Wright. Jimmy was the pre-eminent player in the Met Section during the late 1970’s and 80’s. An eight time Met Player of the Year, Jimmy captured all the major local titles, earned entry into the Metropolitan Golf Association’s Hall of Fame and still holds the Westchester Classic scoring record with a remarkable 62.

Jimmy was succeeded by Jeff Foxx. Jeff won the Nissan Classic in 1984 and the Westchester PGA in 1985. He also played in the US Open in 1984 and the PGA in 1986.

A great course and a rich history have earned Fenway a unique position in the golfing strata. Today, the membership still strives to maintain this tradition. Great efforts are being made to constantly improve and maintain the integrity of the Tillinghast design. His legacy is both the inspiration and the responsibility to maintain for Fenway Golf Club and to the game we love.