The original plans for the Stillwater Avenue course were introduced in 1921 when the Hubbard Heights Inc. organization was formed, according to information kept at the Stamford Historical Society.  It was on March 14, 1922 that the organization voted to finalize the purchase of the land from Mrs. Sallie Roosevelt and Miss Emily Hubbard.  The course originally opened as a nine hole course in 1922, later becoming 18 holes in 1925 under supervision of club professional Michael Began.

Maurice McCarthy Sr. of New York was the original course designer.  McCarthy also designed several other notable clubs, including Knickerbocker CC in New Jersey and Hershey CC in Pennsylvania.  Primarily a golf professional, he also dabbled in architecture.

The course originally was built on 62 acres, but had up to 70 acres, its current size, by 1925.

The golf course became public in 1949 when it was purchased at foreclosure for $165,826.  A private membership course previously, it opened for play to Stamford residents on April 1, 1949.

The first pro at the course was Ralph Miner in 1921, with Michael Began taking over as pro in 1922.  Terry Connors, the former caddy master in the 1930s while the Heights was private and later a golf pro at a 9-hole golf course at Cummings Park, became the first pro/manager at Hubbard Heights when it opened to the public in 1949.  Albert Vitti was the first groundskeeper. Current PGA Professional, Vance Levin, has been the Head Golf Professional here from 2000 to the present day.

The course was officially called the Hubbard Heights Golf Club from its inception in the '20s, until 1978. The name was changed that year to E. Gaynor Brennan, in honor of the former official who was instrumental in purchasing the club in 1949.

Much more detailed history of the course is available through the Stamford Historical Society, including extensive minutes of meetings kept by the Hubbard Heights Golf Club.