In 1901 the founders of Woodland constructed the club's first true golf course a nine-hole layout measuring 2619 yards. By 1907 the club built its first 18-hole course, measuring 5623 yards with nine holes on each side of the railroad tracks. In the 1920s Donald Ross was commissioned to redesign the existing layout.

While Wayne Stiles is the architect of record, there is no question that Ross spent considerable time working on the Woodland remodeling. Ross' contouring, bunkering and routing affected 9 holes. His most important contribution, however, was the course routing, which remained largely unchanged until the early 1960s, and even then was incorporated into the "new Woodland".

In 1960 architect Geoffrey Cornish (noted for his work at The Country Club and Myopia Hunt Club, among others) undertook a massive hole-by-hole redesign of the golf course. "I have been extremely proud over the years to claim that I was associated with the remodeling of Woodland," Cornish noted in 2001, adding that the job was "the first comprehensive remodeling executed in the Boston area" in almost a quarter century.

For the past few years, golf course architect Stephen Kay has assisted in the development and implementation of the golf course master plan. turning the club's 135 acres into a uniquely enjoyable golf course. One hears it over and over: You never get tired of playing Woodland.