The first Ephraim Regatta was organized in 1906 by Henry S. Vail, for whom the Vail Cup is named. The event has been held every year since.  In early years, in addition to sailboat and motorboat races, the regatta included canoe and rowboat races, diving contests, swimming races, canoe tilting, and baby beauty contests. In the Depression years, prizes consisted of homemade fudge, cookies and tin cups instead of real trophies.