March 1987, Perth, Australia: Dennis Connor is retaking the Americas Cup in a 4-0 sweep of the series from Kookaburra. Sailors in Oswego, NY are planning their second season of Wednesday evening PHRF racing. Executives from Apple Computer are introducing the first color Mac and the expandable Mac SE at a Los Angeles conference center. And in the Los Angeles Hilton lobby bar, two Oswegonians are watching highlights of the Americas Cup races, wondering why anyone would want to put a lime in bottle of beer.

As the conversation between OYC members Dave and Marilyn and Apple execs Keith and Vince turned from sailing in Australia to sailing in Oswego a plan began to emerge. In a failed ploy to acquire a spinnaker (with an Apple logo, of course) suitable for a Tanzer 22, a regatta was born. Over the next few months plans for the First Annual Summer Apple Institute for Learning developed.

Meanwhile, back in Oswego, Rosemary Nesbit a college drama professor and local history buff planned OswegoFest, a celebration of Oswego’s history and waterfront. Falling on the last full weekend in July 1987, the celebration included recreations of historical events in Oswego and planted the seeds for Harborfest.

November 1987, Mayor-elect John Sullivan’s wife Charlotte envisioned a grand celebration of Oswego’s harbor. Building on the modest beginnings of OswegoFest, Harborfest was conceived. With seed money provided by the Oswego Yacht Club, Charlotte approached community leaders to organize Oswego’s first Harborfest. The signature event, originally sponsored by the Power Authority of the State of New York, would be Saturday’s world-class fireworks display by the Grucci Brothers.

On the afternoon of Thursday, July 28, 1988 the first SAIL Oswego began. That afternoon an informal race was held with education leaders from across New York serving as crew. Educators attending the Summer Apple Institute for Learning had the opportunity to learn about yacht racing and the latest in educational technology.  Later that evening, opening ceremonies for the first Harborfest began. Over the next two days some 30 boats from Canada and the US competed in the first Sail Oswego, while thousands of Harborfest visitors watched from shore. The Summer Apple Institute for Learning returned for two more summers.

Over the years Sail Oswego has become one of the premiere yacht racing events on Lake Ontario. Drawing boats from both the eastern and western ends of Lake Ontario, as well as some of the inland lakes, Sail has grown to be the largest keelboat regatta on the eastern end of Lake Ontario. Since 1991 Labatts, USA and Eagle Beverage have been the title sponsors.