While working at the Oakley Country Club, Ross had left an impression on the president of the Boston Athletic Association at the time, Edward E. Babb. During an exchange in 1910 between Babb and Joseph L. Wyckoff, a business partner of stationary maker White & Wyckoff in Holyoke, Massachusetts, Wyckoff remarked that he wished to find a man who "really knew about the laying out a golf course" for the Mount Tom Golf Club, today known as Wyckoff Country Club. Babb introduced Wyckoff to Ross later that year, bringing him back to the course, where he suggested key changes, but was unable to prepare plans as he had just signed a two-year contract as professional for the Essex County Country Club. Completing this contract he returned to Holyoke in 1914 where he was put up in a house built for him by Wyckoff, who as an executive committee member of the Massachusetts Golf Association, saw himself as a patron of Ross, and offered him financial backing to move from being both an architect and golf pro, to focusing his career mainly in golf course architecture. It is unknown what duration or regularity Ross lived in Holyoke, as he travelled often, even spending time designing a course in Cuba during his tenure in Manchester that previous year, though a "Boston Herald" article still placed him in Holyoke in 1919. He would work with the Mount Tom Club for many years, welcoming Holyoke neighbors visiting his winter home in Pinehurst, completing a full redesign of the Mt. Tom course by 1922, and later serving as a pallbearer for Wyckoff following his death in 1931. Ross's work in Holyoke would remain largely untouched until the construction of I-91 in 1965 left only 5 fairways of his design today.