Crab Orchard Lake is a 7000 acre body of water built in 1936 and was for a number of years the largest man made lake in Illinois. After World War II the lake and adjacent lands were transferred from the War Department to the Dept of Interior's US Fish and Wildlife Service. The Crab Orchard National Wildlife Refuge was created in 1947.

Sailing began on Crab Orchard Lake in the 1940s and reached peak activity in the early 1980's. In 1958; the first local sailing organization was formed with 7 members and grew to 161 members by 1982.. Until 1985, the Crab Orchard Lake Sailing Club leased land next to the present Play Port Marina. Club members constructed docks, a catamaran beach, storage buildings, restrooms, picnic shelter, a dry sail lot and launch hoist from funds paid by member dues and special collections. These facilities were designed and operated to accommodate day sailors, catamarans, and cabin boats. Several fleets were established. Hobie Cat sailors, with over 50 boats, established Fleet 199 and Flying Scot sailors established Fleet 30. There were also Rebel and Scow fleets. There was also a junior sailing program The Club hosted the multi-fleet Egyptian Cup Regatta which is now held at Carlyle Lake. The Club also leased a portion of the land to the SIU Collegiate Sailing Club which maintained a fleet of 10 Flying Juniors.

After the Club relinquished its lease in 1985 to the private for profit Play Port Marina management, Club social and racing activities quickly died. Membership dropped to 25 and by 1991 membership declined to the point the club finally ceased all activity. Despite the club's absence, sailing still continued on the lake with approximately 30 boats kept on the lake.

In the late summer of 1996, 20 sailors met to discuss the potential opportunity to regain all or part of the sailing harbor facilities. The lake oxvalers, US Fish and Wildlife Service, were publically pursuing changes in the marina operation and sought public input. The group conducted a survey of registered sail boat owners in the region and determined that at least 70 of them would become users of a sailing harbor facility if FWS provided one. This information was presented to a receptive Refuge staff and from this the Crab Orchard Lake Sailing Association was born. By the Spring of 1997, FWS took over the management of the marina including the old sailing harbor area and established a user advisory council. The Association has two members on the council. FWS plan to completely rebuild the marina within the next 3 to 5 years and promise to include sail boat facilities in the plan.

In the Summer of 1997 the Association held its first major social event at the lake with over 60 people attending. In February of 1998, the Crab Orchard Lake Sailing Association held its first annual meeting and began planning a full season of activities.