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Tuesday, January 27, 2026

Gildersleeve Prize

 Ever since Ice Yachts have sailed the Hudson River, there has been racing between yachts & yacht clubs. Even today some ice boaters live just to race against fellow boaters. Whether for bragging rights or a silk pennant, racing brings out exciting moments of speed & drama.  

What are some of the prizes that ice boaters raced for?  Stumbling on an old email thread got me looking back at the races and rewards. 

I've previously posted about one of the most exquisite trophies in ice yachting, The Van Nostrand Cup



I've also covered much of the history of the Ice Yacht Challenge Pennant of America, the 30 foot silk pennant established by Irving Grinnell in 1875.



What spurred this post was an email John Sperr (keeper of the HRIYC.org website)  received from a woman 5 years ago. She had acquired a silver oil lamp trophy at an auction in western NY. 

In lieu of silk pennants and silver Tiffany cups, there is always a race to be had for an oil lamp! 

But what a beauty!  


                    This is the Gildersleeve Prize, awarded to winner of the HRIYC race for third class yachts. 

                                      Third class boats had sail area between 350 -450 sq ft.





       Winner of the race on March 16,1887 was Lewis Edwards' yacht ArrowArrow was 31 feet long with sail area of 369 feet.  

I found a  news clipping of the race in John Roosevelt's scrapbook (from the FDR museum & library archives).  

Edwards, outsailed Edmund Pendelton Rogers ( typo in clipping), sailing Snowflake,  38 ft in length and 444 sq ft sail.  EP Rogers was Archibald Rogers father and secretary of the HRIYC at the time.  


Who was Gildersleeve?  
Judge Henry Alger Gildersleeve was born in Dutchess County and schooled in Poughkeepsie. He was a teacher before entering the Civl War in 1862. He  engaged in campaigns in Gettysburg, the Carolinas and Georgia. He mustered out in 1865 and was noticed for his service by President Lincoln. He became a judge in NYC and was a founding member of the NRA. (yes that NRA).  On the ice, he was a member of the Poughkeepsie Ice Yacht Club, and later, the Hudson River Ice Yacht Club. 
 

                              Ice Yacht Virginia, with owner Judge H.A. Gildersleeve; circa 1880. 


Lewis Edwards kept his yacht Arrow at John Roosevelt's Ice Boat Barn at Roosevelt Point. Roosevelt housed his many boats along with several big boats of Club members.

Judge Gildersleeve had a long, successful, and at times controversial, career. He had the wherewithal to sponsor trophies for races in the 1880s.  



Many thanks to Heather Mulloy for graciously sharing her pictures and for saving a piece of ice yachting history.


And, what other items have been offered up in races?  a very short list of things that I will hopefully add to over time: ( in random order)

Glass cigar holder  for 6th class races at Hyde Park  Feb 1909   won by Comet

Silver Salver 1869 Haze Aaron Innis

silver pitcher 1871 Ella   T.V. Johnston

Club plate  1872  Haze

Silver Plate  1872  Artic Jacob Buckhout

Silver Tiller 1881  Icicle  JAR  

And, my favorite:

circa 1888  4th class race of NHIYC boats;  won by Puff;  quoting the Pok Eagle: "This was a flour race. Only 4 boats sailed in the 4th class, giving every non-active member of the club a barrel of flour." 

And loving cups of all shapes and sizes and designs:



Medals awarded to skippers winning the Ice Yacht Challenge Pennant of America"

Phantom 1881


Icicle 1899

Jack Frost 1893
 





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