… as recounted by Bill Transue, Jr. and listed on a previous PSYC web site:

There was actually a race in 1966 between Art Totman in his lightning and the Transues (Bill Sr and Jr.) in Elsewhere.   But fog rolled in and nobody finished, but, fortunately, nobody stayed lost.  The next year saw the same two boats.  I think Elsewhere won, but I wouldn’t swear to it. The next year brought two more boats from Jonesport belonging to the Fishes (Harry Jr. and Sr.) and Russell Batson, who won, demonstrating that where to go when was quite important. In the ensuing years the regatta had good participation. Art Totman was a driving force, and Dr. Karl Larson was a steady participant. I can’t remember exactly when the name ‘Port and Starboard was introduced.  Maybe Art Totman, maybe Ellen Farnsworth, maybe one of the Fishes might remember that.

It seems to me that there were a few races with as many as 14 boats.  Wally Kurz was a participant for a time, and after his death the race was named for him.  Once we had a very snazzy finish line marked by two small identical buoys. That time I remember groping through the fog and finding one of them— trouble was we weren’t sure which one, so we circled it both ways to be sure of having crossed.

The race has had many boats, some big— John Bryfogle’s
Islander, a big wooden cutter. A good sized schooner brought by Ken Rich, Pisces and Kittiwake from Jonesport, Jim Wells’ boat Windswift from Perry, Spectrum brought by New Yorkers Sandy and Pip Wurmfeld, whose son Jeremy has designed the e-33 (check it out on the web!).  People from around here who have raced include
Mike and Kathy Carter,  Jim and Phil Mayhew, Jeff Huntley, Dana Urquhart, Dick Jacques, Dave and Robin Rier, Harper Dean, Arthur Hill,  Ed Cates, and Kenneth Wood

I just found newspaper clippings from four regattas 1977 (10th, 11 boats),1983 (16th) 1987 (20th) and 1990 (23rd,11 boats).