Falcon won its fifth Maine Retired Skippers Race last year. Launched in 1936 and still racing in her 83rd summer, the Sparkman & Stephens-designed New York 32 has had strong finishes in this year’s Camden Classic Race and Eggemoggin Reach Regatta. FILE PHOTO

Maine Retired Skippers Race set for Saturday

CASTINE — The Maine Retired Skippers Race is scheduled to get underway Saturday afternoon at the entrance to Castine Harbor.

It will be the 68th edition of the event aimed at graybeard sailors, or at least sailors of any gender old enough to qualify as old salts.

As of Monday morning, 12 boats had signed up for the race, most of them using the high-tech regattaman.com website, but the fleet could grow by Saturday’s 1 p.m. starting time.

Murky weather held last year’s fleet to an even dozen but, in years past, it was not uncommon for more than 20 boats, many of them skippered by retired professional mariners, to come to the starting line.

The Retired Skippers Race fleet comprises a variety of cruising boats at least 25 feet in length helmed by skippers who are at least 65 years old.

In the event’s earliest days, the skippers had to not only meet the age requirement but had to have been born in Maine or at least lived in the Pine Tree State for several decades.

The passage of time took a toll on the number of sailors who could meet those qualifications, so now eligibility for Social Security is the only requirement.

The format of the event is a pursuit race, in which the slowest boat, based on assigned handicap, starts first followed in order by the faster boats. Each skipper’s objective is to pass all the boats that started ahead and to be first across the finish line. In theory, if the handicaps are correct, the entire fleet should finish the race tightly bunched, but theory and reality often collide.

The five-leg race is sailed over a 12-mile triangular course in eastern Penobscot Bay with the starting line set at the entrance to Castine Harbor. Two turning marks are set off the Islesboro shore, and the race proceeds clockwise or counterclockwise, depending on the wind direction.

Since its inception, the purpose of this race has been to allow retired skippers to show their boat handling skills at the helm of sailing vessels designed primarily for cruising. While race boats are not expressly excluded, each vessel is expected to contain full cruising amenities for a boat its size.

First sailed on Eggemoggin Reach in the autumn of 1952, the inaugural race featured two genuine retired blue-water skippers, each taking the helm of identical Controversy sloops designed by E. Farnham Butler of the Mount Desert Yacht Yard.

Captain Frank Delano represented Bucksport in Controversy. Captain Phillip Haskell sailed for Deer Isle in Consequence.

Haskell won, and presented Delano with a clam hod, “so that he could earn his living digging clams,” as a consolation prize. Haskell himself won the Captain Henry Whitney Challenge Cup. To this day, the Whitney Cup and the clam hod remain the prizes for the first place and last place skippers in the race.

The first few races were sailed in different venues — on Eggemoggin Reach or Blue Hill Bay and off Mount Desert Island. Since 1960, the race has been sailed on Penobscot Bay and hosted by Maine Maritime Academy.

Stephen Rappaport

Stephen Rappaport

Waterfront Editor at The Ellsworth American
Stephen Rappaport has lived in Maine for nearly 30 years. A lifelong sailor, he spends as much time as possible messing about in boats. [email protected]

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