When the Cambridge Golf & Country Club moved to Strawberry Hill and commissioned Willie Campbell to lay out 18 holes in 1898, the course became the first 18-hole layout in Massachusetts. The club changed its name to Oakley Country Club later that year. In the summer of 1898, grounds committee member and Harvard professor Robert W. Willson recruited Donald Ross from Dornoch; Ross arrived in spring 1899 to teach, make clubs, and soon to serve as greenkeeper.
Changes in Oakley’s landholdings during 1899—some parcels acquired, some leases lost—required a swift re-planning of the young course. Campbell’s declining health prevented his return, and the club assigned the redesign to Ross, then untested as an architect. According to the club’s history, Ross completed his first Oakley redesign for play by the fall of 1900; a Ross plan labeled “1900” is cited as held in the Tufts Archives. From 1899 through 1910, while serving winters at Pinehurst and spring/fall in Watertown, Ross repeatedly refined Oakley’s routing and features. The last documented redesign occurred in 1910, when, after the club acquired the adjacent Payson Estate, two replacement holes were constructed “according to plans previously designed by Mr. Donald J. Ross.” The club presents the post-1910 routing as unchanged to the present.
The club’s narrative also attributes early infrastructural advances to Ross’s tenure, noting water to greens and tees by 1900. Contemporary newspapers and club records describe Oakley hosting Harry Vardon for a 36-hole exhibition in 1900, and Oakley’s early prominence is underscored by the inaugural Women’s Golf Association of Massachusetts Championship held there that same year.
Unique Design Characteristics
The property’s identity rests on Strawberry Hill’s topography and the economy of routing within a compact boundary. Ross’s Oakley takes golfers up and over the hill repeatedly, using elevation as the primary hazard. The 3rd (“Over the Top”) is a steeply uphill par 3 where the recommended play is up the left to allow the slope to feed the shot—a microcosm of Oakley’s demand for controlled trajectory. The 16th (“Coronary Hill”) is a long-playing uphill par 4 by the clubhouse, where tee balls must navigate cross-bunkers to earn a favorable approach into a green that runs away, emphasizing angle and ground use rather than forced carry alone.
Bunkering that works diagonally across lines of play remains a hallmark of the current course, with the 10th (“Water Hole”) offering perhaps the clearest example: the preferred play is to choose between laying up short of, or carrying, a pair of cross-bunkers before confronting a tiered green. The club’s hole notes also draw attention to strategic cross-bunkering on the 16th and a prominent cross bunker three-shot decision on the 13th, indicating that the present bunkering scheme—realigned in the mid-2000s using century-old Ross drawings—continues to enforce angles and decision-making rather than simply distance.
The greens present a catalogue of specific challenges: a pronounced false front at the 11th that repels under-struck approaches; the 14th’s elevated surface that runs markedly from back to front; and the 12th’s short target that sheds balls hard right-to-left. The 7th is described as a “very contoured” uphill target, and both the 9th and 18th play over fairways and greens that tilt left-to-right, creating a persistent need to shape shots into slopes. These hole-by-hole traits, whether original surfaces or restored to historic dimensions, are consistent with the club’s stated goal of realigning bunkers and greens to Ross’s plans during the 2004–06 work. As representative survivors of Ross’s ideas on this site, the 10th (for its cross-bunkers and tiered target), the 11th (for its false front), and the 16th (for its uphill cross-bunkering and canted green) are the clearest.
Historical Significance
Within Ross’s corpus, Oakley is foundational. It was his first American club appointment, the place where he shifted from professional/greenkeeper to designer of consequence, and—per the club’s record—his first completed redesign project, finished in 1900. The Ross Society and The Cultural Landscape Foundation both summarize this stage as the Boston-area beginning of a career that would soon migrate to Pinehurst each winter, but Oakley was the proving ground where Ross iterated on a real course across more than a decade.
Oakley also functioned as a regional stage. The club helped found the Massachusetts Golf Association in 1903 and the Women’s Golf Association of Massachusetts in 1900; it hosted the inaugural WGAM Championship that year and later staged the Massachusetts Open in 1912, which former Oakley professional Alec Ross won. The timeline further notes exhibitions and play by figures such as Harry Vardon (1900), Franklin D. Roosevelt as a Harvard student (1901–04), Bobby Jones during his Harvard years (1923), and John F. Kennedy (1937) with the Harvard freshman team. While these claims come from club-curated history citing contemporary newspapers, they track with Oakley’s status as a centrally located, early Boston-area hub.
Current Condition / Integrity
The club asserts that the routing has remained “identical to the last Ross re-design in 1910.” In 2004, Oakley engaged restoration architects to review century-old Ross documents and realign bunkers and green perimeters to the drawings, with the bulk of that work completed by 2006. Public-facing course directories attribute more recent course work to Ron Forse (often alongside Jim Nagle and/or Stephen Kay in aggregate listings), which aligns with Forse Design’s broadly documented restoration portfolio, though the club’s own site does not name the firm. In practical terms, the present course plays as a ~6,000-yard, par-71 (in most listings) with cross-bunkers and green contours on key holes that support the club’s claim of adherence to the Ross plan.
Where preservation is strongest appears to be in the routing over Strawberry Hill and in specific green/bunker relationships that still dictate play: the 10th’s tiered green beyond cross-bunkers, the 11th’s false front, and the uphill tests at 3 and 16. Elements that are less certain in their Ross provenance include the water hazard fronting the modern 15th, and the exact historical extent of tree planting that now frames approaches at holes such as the 8th—points that are not resolved in publicly accessible sources. Without direct access to original Ross plans and construction notes, or to early aerials, the degree to which certain hazards (e.g., the pond at 15) or tree corridors reflect 1910 conditions cannot be stated conclusively here.
Sources & Notes
Oakley Country Club, Club History (timeline and narrative; includes citations to board minutes, newspapers, and a 1900 Ross plan at Tufts Archives). Oakley Country Club, Golf (hole-by-hole descriptions, yardages, scorecard images section).
Mass Golf, “Member Clubs Celebrate 125 Years” (background on 1898 Willie Campbell 18-hole layout at Oakley and early Massachusetts 18-hole courses).
The Donald Ross Society, “Donald Ross Bio” (Ross’s arrival in Boston in 1899 to build/run Oakley).
The Cultural Landscape Foundation, “Donald Ross” (Ross’s move to Oakley in 1899; context for early career).
Club + Resort Business, “Oakley CC Takes the Long View with $8.8M Clubhouse Renovation” (2018–19 clubhouse work; context for current facilities, not course design).
PartySlate venue page for Oakley (reiterates 2004 restoration to Ross plans and 1910 routing continuity; secondary confirmation of club statements).