The Woodlawn Sailing Club was formed in 1939 on Woodlawn Lake. It is the home of one of the earliest Sunfish Fleets (#32) in the U.S. Other one design boat charters are the Snipe (#140) and the Windmill (#25). Due to the size of the lake, it is primarily used for board boat and centerboard boats as well as Radio Controlled Sailboats. Many San Antonio sailors began sailing in Woodlawn and then progressed to larger boats on other lakes and have gained national recognition as sailors, judges, and race committee management.

Woodlawn Lake is a wonderful place to experience the sport of sailing in San Antonio whether it be from the shore with a radio control or in a small boat. This is a family oriented experience and children as well as adults enjoy it with the camaraderie of true sailors. Events include regular practices as well as annual regattas hosted by the club. The lake lends itself to being a very safe body of water to learn to sail for sailors of all ages.