The OIYC has a very active racing schedule. Racing events include the Shaw Island Winter Classic, the April WSSR, the Friday night races running from May through the end of August, the September Sunday afternoon series, the Benson Cup, and the big finale of the season, the Round the County Race. The club makes good use of West Sound for many of its events. With its protected waters, which are out of the main flow of heavy currents and a good chance of usable wind even during the summer months, West Sound is a fun place to sail and still gives a little advantage to the old-timers who know its shifty ways.

The early races of the season can be lightly attended, but by July and August more than 20 sailboats may be seen out racing on a Friday night. After the racing is over, a good time can be found at the OIYC picnic shelter, where the racers gather to grill their dinner, drink their beer and talk about the rules of racing, which clearly the other skippers don't have a clue about.