On a Sunday in February, 1968 at Mike's Black Stallion Tavern in Olcott, several locals sat talking of the rigors of winter and their ability to scoff at its harshest impacts. As often happens, a couple of the more boastful patrons challenged the willingness of the other to demonstrate the strength of their words by jumping into the frigid water of Lake Ontario. It is unclear what was said next, but that afternoon seven hardy souls took the plunge.

The next year, Black Stallion owner, Mike Rann, decided to capitalize on the previous year's spontaneous pastime and formed a Polar Bear Club that started the annual dip as a winter tradition. The number of swimmers and hoopla associated with the swim expanded quickly in the early years. The first swim took place in the harbor adjacent to the tavern at the west end of Ontario Street, but was soon moved to the Krull Park beach. The tavern was torn down in the 1980s, but many early participants remember the times when swimmers would gather at the Black Stallion, to be led by a brass band to a waiting throng of spectators on the Krull Park terrace.

For many years the swim remained linked to the Black Stallion and swim founder, Mike Rann, but the swim rapidly grew to become associated with Olcott as a community event, most commonly referred to as 'Polar Bear Day'. It did not take long for organizers and entrepreneurs to recognize that money could be raised from the swim, and even the early swims that centered around the club and tavern raised proceeds for charity Through the years, street and food vendors, carnivals and amusement rides, 'snowball' softball and volleyball tournaments have all been part of a one to three day swim weekend. The event has often been billed as the world's largest polar bear swim.

The Olcott Lions Club started helping with the swim and fundraising in the early years and swim founder, Mike Rann, has been an active, long-time member of the Lions. No one can pinpoint when organization of the swim passed from Mike and the tavern to become a Lions activity; most think it probably occurred gradually and cooperatively over many years. It was not until 1998 that the Lions Club started to keep records for the swim and at the same time adopted a format similar to the walk-a-thons, where swimmers are asked to seek sponsors and contributions. Swimmers have responded to this appeal in a huge way making the swim one of the most successful local charity events. Since the early years, the swim has grown from an average of 200 swimmers annually to more than 300, and contributions from swimmers and supporters that aid Lions sight and community needs have multiplied more than six fold.