The Club & History
A BRIEF HISTORY OF THE OAKLEY COUNTRY CLUB
The Club traces its roots to 1895 when it was established by a group of prominent men mostly from the Brattle Street area of Cambridge. It was initially called as The Cambridge Golf Club. The original 9 hole layout was located on the old Adams estate at Mt. Auburn and School Streets in Watertown, MA, just south of the present course. In 1897 members of the Club acquired from the estate of William Pratt, the former Harrison Gray Otis country estate: "Oakleigh" together with its Charles Bulfinch designed mansion as its new clubhouse. Located on historic Strawberry Hill, the highest point in Watertown, Otis' Oakleigh enjoyed views down the slopes to Boston and beyond to the Atlantic Ocean. Today, Oakley visitors still marvel at its breathtaking vistas of the Boston and Cambridge skylines.
In February, 1898, the Club incorporated as The Cambridge Golf and Country Club and engaged noted Scottish player and course designer Willie Campbell, who had previously laid out a nine hole course at The Country Club. Campbell set about designing the first 18-hole course in Massachusetts. This was followed in late 1898 by Mypoia, and then in 1900, The Country Club added a second nine to its historic track at Clyde Park. In November, 1898 the Club changed its name to The Oakley Country Club.
Club Grounds Committee member and Harvard Professor, Robert W. Willson (two L's please), during a trip to Scotland in the summer of 1898 and with the blessing of the Club Board, recruited 27 year old Donald James Ross from the Royal Dornoch Golf Club to come to Oakley. Ross arrived in the spring of 1899 initially to work as golf instructor and clubmaker. In his first year Ross' duties expanded to include greenkeeper as he worked feverishly to get the new Campbell course in shape. During 1899, the Club's land configuration changed as some new property was acquired while some leased land could not be renewed. Sadly, Willy Campbell could not work on a re-design due to his poor health (he died from cancer on November 25, 1900 at the age of 38).
Oakley turned to young Donald Ross who had clearly impressed Club leadership during his first year. The Club gave Ross (then untested as an architect) the assignment and he completed his first re-design of Oakley by the 1900 fall season. Ross was able to send $2,000 home to his mother in Scotland that year[xvi]. She used much of this money to add a second story to the home where Ross grew up on St. Gilbert St. in Dornoch. His mother was so grateful for the opportunity the Club gave her son that she renamed the family home "The Oakley Cottage". Over his 11 years at Oakley, Ross honed his layout skills re-designing the course several times making Oakley into a classic, tight, park layout: complete with the challenging bunkers, cops and fast, undulating greens for which he is now universally renowned.
The Club grew rapidly as its close proximity to Boston and Cambridge allowed for easy access. Oakley engaged Alec Ross (Donald's younger brother) as an additional pro to help with lessons in 1900.  Oakley quickly earned a reputation as a quality golf course as evidenced by its hosting Harry Vardon during his famous 1900 US tour. A few weeks after his US Open win that year, Vardon paired against Ross and fellow Scotsman, Alex Findley, for a grueling 36 hole match which Vardon won 6 and 5 . Vardon declared after the match that the Oakley course was "one of the finest in the Country".
Donald Ross's personal golfing accomplishments were impressive. Ross placed in the top ten at the US Open three times from 1903 to 1907 and 8th at the 1910 British Open. Ross won the inaugural Massachusetts Open in 1905, and then again in 1911. From 1905-1912, Donald Ross and his brother Alec won every Massachusetts Open Championship, including 1912 when Oakley hosted this prestigious event.
Oakley was a founding member of the Massachusetts Golf Association in 1903. Oakley was also one of the four founding members of the Woman's Golf Association of Massachusetts in 1900. The Club hosted the inaugural WGAM Championship that same year, and has hosted it five additional times. Oakley women golfers were dominant in the first half of the 20th century. Members Pauline Mackay and Katherine Harley Jackson won the US Amateur, while Oakley women have won 16 Massachusetts Amateurs including Edith Baker who won the event 5 times!
In 1900 Ross became the "Winter Pro" at Pinehurst CC, and continued as the "Summer Pro" at Oakley until 1910. The term Summer Pro is a bit of a misnomer as Ross actually worked at Oakley from about March to early July, then again from about September through November. July and August saw most prominent clubs near US cities all but abandoned in the hot summer months during this era as most members retreated to their summer residences near the shore or mountains. Ross rose to national prominence in 1907 with his design and completion of the second 9 holes at the famous Pinehurst No. 2 course. Ross pioneered many golfing innovations during his days at Oakley. By 1900, he had water plumbed to all greens and teeing grounds. In 1905 he instituted indoor golf lessons at the Oakley squash courts. In this teaching role, Ross transcended the servant / master relationship common at many country clubs during this period. Ross developed lasting friendships among many of the prominent Oakley members. Several of these relationships led to new course design contracts near the members' summer homes and ultimately to his amazing career: over 400 golf courses are attributed to Donald J. Ross! After his time at Oakley, Ross largely gave up competitive professional golf and never competed in another Major. His new focus was teaching golf, and golf course design. By the 1920s he was almost exclusively focused on the latter.
In addition to Donald Ross, Oakley has been blessed over the years with a number of talented Professionals. Alec Ross was an Oakley pro together with his brother Donald from 1901-c1903. He won the 1907 US Open. Michael J. Brady was the Oakley Professional when he placed runner-up in the 1919 US Open. He was also runner-up in the 1911 US Open. Brady was a nine time PGA event winner between 1916-1926. John Cowan was the Oakley Pro when he was runner-up in the 1921 New England PGA and in 1923 when he was Champion. Famous former Oakley assistants include Skip Wogan, the longtime Essex pro and Chris Callaway, a long serving Pinehurst professional. Oakley's current Pro, Scott Johnson, his predecessor Jeff Bailey along with former Oakley Pro Paul Donahue together share the current Oakley Course Record at 64!
Other Oakley members have enjoyed success as well. Member Joseph G. Thorp finished runner up in the 1896 US Amateur. Member Alfred Ripley bested perennial Amateur champ Walter Travis in the 1898 Shinnecock Hills Consolation Cup and would later set that course's record in 1902. Former Oakley caddy, then member, Fred Wright won the 1956 US Senior Amateur. He still holds the record for the most Massachusetts Amateur wins at seven. The Club continues to honor Mr. Wright's memory with its Spring Member–Guest Tournament, which is named in his honor. While serving as Club President, Mike Ohanian won the Club Championship as well as the Massachusetts Amateur Championship in 1968!
The original Oakley Clubhouse was tragically lost in a 1960's fire. It was replaced by a new clubhouse, remodeled in 1998 to be faithful to the lines of the original Bulfinch building. The 2018-19 clubhouse renovations further the Club's effort to continue the charm of a New England country estate while providing best-in-class country club accommodations. The course layout itself has remained identical to the last Ross re-design in 1910. The Club engaged restoration architects in 2004 to examine the century old Ross designs and realigned the bunkers and greens to the Master's plan. This extensive undertaking was largely completed in 2006, but is an ongoing Club project. As a city club, Oakley is land locked. Our 85 precious acres allow for an amazingly efficient 6,000 yard course primarily because our architect's greatest gift was his ability to route fairways!
We welcome your visit to Oakley. Previous Club guests have included several US Presidents: Teddy Roosevelt, Franklin D. Roosevelt and John F. Kennedy. At the end of TR's 1905 visit, newspaper accounts report that he declared: "Oakley… is a perfectly bully place, and we all had a good time!" Legend has it that former US Senator, Boston Mayor and famous entertainer H.G. Otis hosted numerous US Presidents and dignitaries at Oakley in the early 1800s including John Adams, James Madison, James Monroe, J.Q. Adams as well as the Marquis de Lafayette. We believe Oakley is a historic venue of "good times" that continues to the present day!
Rev. 2.8.19: Oakley Historical Committee, D.O. Mee, Chair.
 The Golfing Annual 1899=1900. Edited by David S. Duncan. Volume XIII. London: Horace Cox. Page 160.
 Walks and rides in the Country round about Boston, EM Bacon, Houghton Mifflin & Company , 1898, pp 212-213.
 Cambridge Chronicle, December 11, 1897, p 15.
 Genealogies of the Families and Descendants of the Early Settlers of Watertown, Little Brown, 1855 p1031
 Oakley Country Club Yearbook, Addison C Getchell printer, Boston, 1899, Title page.
 Cambridge Chronicle, March 12, 1898
 Boston Sunday Globe, April 2, 1899, p 36
 Oakley Country Club Yearbook, Addison C Getchell printer, Boston, 1899, Title page.
 Oakley Country Club Yearbook, Addison C Getchell printer, Boston, 1899, p. 4
 Correspondence between DJ Ross and WB Durant, April 22, 1937; Correspondence between DJ Ross and RA Young, November 19, 1947
 The First Hundred Years 1898-1998, A Special Legacy. Oakley Country Club Centennial Book, 1998, p13
 https://en.wikipedia.org/wiki/Willie_Campbell_(golfer)#Death "Famous Golfer Dead". Boston Evening Transcript. 26 November 1900.
 1900 Ross plan of Oakley. Tuffs Archives -Given Memorial Library
 "Golf Never Failed Me" by Donald Ross pp. 9-11
 Correspondence between EP Shapiro and D Shea, January 4, 1998.
 Boston Sunday Globe, August 5, 1900. P.27
 Boston Dailey Globe October 17, 1900, p.5.
 Boston Post, 11.11.1900.
 American Golfer, July 1910, P. 252
 Ibid p.22[xxiv] Ibid., p.276
 The Architechts of Golf, GS Cornish, Harper Collins,1993, p. 420.
 "Virtual Golf Course: Pinehurst – Donald Ross's Masterpiece
 Boston Dailey Globe, September 2, 1900, p. 31
 The First Hundred Years 1898-1998, A Special Legacy. Oakley Country Club Centennial Book, 1998, p23.
 Boston Globe, August 5, 1900
 NY Times Aug 6 1902.
 Mass Amateur media guide
 Oakley Board Minutes, 1912
 Boston Sunday Post August 9, 1908