According to Harper's Official Golf Guide of 1900, Fenwick Golf Course was 2,550 yards long, annual dues were $10 and there were 85 members. F.E. Cooley held the amateur course record of 42. The president (and the individual who laid out the original golf course) was J.B. Moore, the secretary was M.B. Brainard, and the green-keeper was John Graveson.
By the end of 1900, golfers throughout the United States knew about Fenwick because the 1898 U.S. Amateur champion, Findlay Douglas, played in the first Fenwick Open in 1900.
Douglas, of Fairfield Country Club, now Greenwich Country Club, had won the U.S. Amateur in 1898 and finished second the next two years. In 1900 he lost to Walter Travis at Garden City Golf Club, before competing at Fenwick.
After 1900, the members appeared to be content to just enjoy Fenwick, and it never hosted a tournament of that caliber again.
The course Douglas and the members played in 1900 had many similarities to the Fenwick of today. On the other hand, the greens were larger and had more square corners, and the grass on them was longer and less uniform than today.
In 1900, Connecticut Magazine described Fenwick this way: "Some of the hazards are wonderful country roads that have been built along the river and Sound and are made of vast quantities of sand, four times as much as are necessary, with a variety of cacti along the sides. If this was not enough, sand dunes have been built, ditches have been dug and partly filled with sand and there are artificial bunkers."
The condition of Fenwick has improved substantially since those days, but there are some traits that have been here since the course opened and are the defining characteristics of the course such as the berms on the second, fourth and sixth holes, small greens, wide hole corridors and firm fairways and greens.