In 1920, the members of then Fenimore Golf Club enlisted legendary golf course architect Devereux Emmet. Not long after its introduction, the members determined that the Emmet design did not fulfill their goal of establishing a truly championship caliber course.  At that point the club retained the services of the A.W. Tillinghast, who was then designing neighboring layouts at Winged Foot and Quaker Ridge.

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“Tillie's” design featured a strong dependence upon the natural terrain along with heavily bunkered greens of various dimensions. When Fenimore re-opened in 1924 its new course was immediately crowned a smashing success. 

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During its first decade, Fenimore became one of the first clubs in the country to employ a playing Tour professional as well as a standard club professional. Leo Diegel, who won back-to-back PGA Championships in 1927 and 1928, was among the club’s notable playing pros. During this period, "Wild" Bill Mehlhorn, a member of the PGA Hall of Fame. A winner of 20 PGA tour events and Diegel's counterpart on the Inaugural United States Ryder Cup Team manned the club's Pro Shop.

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With the nation suffering through the Great Depression, Fenimore's members found themselves struggling to maintain the club's financial viability.  The club was forced, in 1936, to reorganize as Fenway Golf Club.