Chequessett was established on March 18, 1929 as the Chequesset (note one “t”) Golf Club. Unfortunately, within 6 months the U.S. stock market crashed, wages were low, unemployment was rising, and debt was growing. This was hardly the time for investing in a club membership. Chequesset membership was equity-based, relying on purchase of stock at $100 per share. Only 224 shares of stock were sold and some of these shares were not paid for with cash, but rather with goods or services. The oil painting by Gerritt Beneker, currently hanging over the fireplace in the Clubhouse was obtained for 5 shares of stock. These shareholders became the first club members.
Just 5 years later, in 1934 Chequesset Golf Club shareholders hoped to attract new members by encouraging members of the Wellfleet Yacht Club to try anchoring their boats in the waters off Chequesset Golf Club rather than the waters further down Mayo beach at the Chequesset Inn. By 1936, the club added tennis courts and the name was changed to the Chequessett Country Club. Two years later, the Great New England Hurricane, one of the deadliest and most destructive tropical cyclones to strike the northeast demolished the Chequesset Inn and the Wellfleet Yacht Club took permanent anchorage at Chequessett. The club was renamed the Chequessett Yacht and Country Club, offering golf, tennis and sailing to its members.
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.