Much like the Lake itself, the Race has an interesting history. The Race's origin can be traced back to the running boom that swept the country in the seventies. The Woodbury, CT based Tin Man Athletic Club staged the initial running around the frozen lake in 1980. Lead Pack Sports took over organizational efforts and they were followed by the Bethel Bananas Running Club in 1986.
From 1987-1991 what had been the area's only winter running race went into hibernation and the race was not held for 5 years. In 1991, Wallie Jahn opened a retail store for runners, Road & Track Sports, and in response to strong interest from the local running community, he resurrected the Race in 1992 with the help of the Lake Waramaug Country Club.
After Jahn fell ill, Dave Dunleavy stepped up to help manage the Race in 2012. A long time Kent resident and running enthusiast, Dunleavy continued to build on the tradition that has made the Polar Bear Run a favorite of area runners. In 2018, Dunleavy handed off the race organizing responsibilities to Stephanie and Ed Raftery, co-founders of TrailHeads, a Kent, CT based online retailer of gloves, hats, headbands and related accessories for running and outdoor enthusiasts. 2018 also marked the start of a partnership with Guiding Eyes for the Blind as the event's charitable beneficiary.
The current record holders for the Lake Waramaug Polar Bear Run are:
- Men's Record Holder: Elijah Kitur / 38:07 (1998)
- Women's Record Holder: Anne Hird / 43:34 (1983)