Chequessett was established on March 18, 1929 as the Chequesset (note one “t”) Golf Club. Timing was poor as the October 1929 crash came a few months later. Needless to say it is no surprise that only 224 shares of stock, at $100 per share, were sold and some not for cash but in kind and services. The wonderful oil painting by Gerritt Beneker hanging over the fireplace in the Clubhouse was obtained for 5 shares of stock. These shareholders became the first club members.
In 1936 the name was changed to Chequessett Country Club as tennis courts had been laid. And in 1934 the Wellfleet Yacht Club, which had anchorage at the Chequesset Inn, was asked to try our anchorage. The Club hoped to attract new members through this sailing group. The hurricane of 1938 demolished the Chequesset Inn and the Wellfleet Yacht Club took permanent anchorage here at Chequessett.
Activities in the 60′s and 70′s revolved around the young families who made up much of the membership. Sailing lessons, tennis tournaments, and Friday night dances became part of the social life of teenage Wellfleet. Many of those teenagers are club members today and their children are now the young heartbeat of Chequessett.
Staff was very light in the early days of the Club. Tennis “pros” were usually college students, and whoever was managing the club often lived on the second floor of the clubhouse. Groundskeepers who had little golf course training but much “Yankee” ingenuity managed the golf course, a Van Kleek and Stiles design. Today we have certified PGA golf Professionals as well as certified tennis professionals. A GCSAA Class A Superintendent now manages our golf course.
While we have worked hard to become more professional in our management and our teaching, we have also worked hard to maintain the friendly, laid back club that has now existed for over 80 years. Come join us and experience Chequessett first hand.