Initially founded on the Poplar Islands in the Chesapeake Bay. The island of the group was named Jefferson Island. Beneath oaks and poplars, a graceful white clubhouse stood, containing eleven bedrooms and a Presidential Suite. Fishing and hunting were popular pastimes.

President Franklin Roosevelt spent many of his favorite hours at the club holding court under an old mulberry tree. On one weekend he hosted over 450 Senators, Congressmen, Cabinet members and members of the Supreme Court. Whether conferring with leaders of the government and his close advisors or entertaining large parties, Roosevelt utilized the paneled clubhouse frequently, as did President Harry S Truman, who often rose early to fish after an evening of card playing.

A fire in 1946 destroyed the clubhouse and the club's board of governors purchased the site of today's club on St. Catherine's Island. This island is larger and closer to Washington than the site of the original club and is located a mile from the mainland near the confluence of the Wicomico and Potomac Rivers.

President Truman continued to visit the Island for special occasions and parties for many years as did Speaker Sam Rayburn, senator Claude Pepper, Bernard Baruch, Justice Hugo Black, Cordell Hull and many others.

President Truman enjoyed playing cards at the island. No one argued with him during this game!

Though the old flags still flew over the Island during the Eisenhower Administration, the club lost some of its prestige. There was little glamour during Ike's day of belonging to a club whose original stock certificates stated that a member had to be "a male member of the Democratic Party." Subsequently, both John Kennedy and Lyndon Johnson were members of the club but times were changing and with those changes came changes in the Jefferson Islands Club.

In 1977, Congressman Dante Fascell was elected President of the club and began re-establishing its old political traditions, this time on a non-partisan basis. The objective of operating a facility where members of the legislative and executive branches of government can relax and mingle, on an informal basis, with members of the business community was re-instated. These same objectives were pursued by Representative Bill Chappel of Florida who succeeded him as president. Membership of the club has continued to expand and has continued to be led by individuals of prominence and dedication to its goals.

In addition to providing a place for individual relaxation, Jefferson Islands Club hosts several social functions each year. On the island, members and their guests are invited to a Crab Feast in the summer where they are treated to tables of spicy steamed Chesapeake Bay Blue Crabs, crab cakes, and crab gumbo.

In the fall there is an Oyster Roast featuring the "king of shellfish" raw and cooked every way imaginable.

A State of the Union Reception and a Wild Game Buffet are also held in Washington during the winter. Delicacies such as venison, wild boar, duck and geese are donated by club members for the meal.

Another function held in Washington is the Citizen of the Year Award dinner. Recipients of the award have included President George Bush, Rep. Dante Fascell. Speaker Denis Hastert, Majority Leader Steny Hoyer, Speaker Dan Rostenkowski, Rep. Joe Barton, Senator Robert Byrd, Senator Trent Lott, Rep Don Young, and Rep. John Dingell.