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The original plans for the Stillwater Avenue course were introduced in 1921 and opened for play in 1922, according to articles published in The Advocate. It originally opened as nine holes and become 18 holes in 1925. However, a former Hubbard Heights golf chairman, Joe Sherman, later told The Advocate the land for the course was purchased in 1928. This information could not be confirmed, but seems inaccurate in that a report from The Advocate in 1925 had information of a now clubhouse being built at the site. The Metropolitan Goff Association did not have an exact year when the course opened.Maurice McCarthy Sr. of New York. 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 (about the price of a two-bedroom condominium today). Originally a private course, it opened for play to Stamford residents on April 1, 1949.

The first pro at the course was Michael Began in the early to mid-1920s. Terry Connors, the former 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 '49. Albert Vitti was the first grou ndskeeper.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 '49.