John Aspinwall Roosevelt (FDR's Uncle) was the first Commodore of the Hudson River Ice Yacht Club founded in 1885 at Poughkeepsie, NY. His prestigious ice yacht called "Icicle" required a railway flat car to transport and was the largest ice yacht ever built. Nearly 140 years later it is still recognized by the Guinness Book of Records as the largest official ice boat ever built. During the hay day of this gentlemen’s sport, it was built specifically for John A. Roosevelt for racing on the Hudson River in 1869. It was nearly 67’ long and carried over 1000 ft² of canvas.

In 1871 this large vessel beat the "Chicago Express" train on a run between Poughkeepsie and Ossining. Early ice yacht clubs spent most of their time racing trains. In even a modest breeze, the fastest boats could reach speeds of up to 75 miles per hour, easily outpacing the trains heading to and from New York City along the Hudson's East bank. This version of icicle was largely built for bragging rights as it was not allowed to race officially due to it’s non-regulation size. Subsequently a smaller version of Icicle (50’ in length, 750 sq ft sail area) was built to meet the specifications of racing. With this boat John was able to win the Ice Yacht Challenge Pennant of America four times.

The competition with Icicle was an expensive variation on "keeping up with the Joneses " according to Mr. Bielenburg (FDR Historian). In seven races between 1887 and 1902, the Ice Yacht Challenge Pennant of America—the Iceboating equivalent of the America's Cup—changed hands between the Roosevelts and the Rogers four times.

Iceboating declined in popularity after the turn of the century for several reasons, one being that these families in later generations moved to places such as Newport, and another being the ice breakers which began regularly working the Hudson starting in the 1930's. Furthermore, recent decades have seen a warming of the region's climate shrinking the stretch of the Hudson that freezes thick enough to support the boats.

Most ice-boat racing is now achieved on lakes such as Orange Lake, Greenwood Lake, and Saratoga Lake. There is a regatta on the Hudson in Tivoli Bay when the ice is more than ten inches thick, but it is more of a social event than a racing meeting. Photos: Iceboating enthusiasts took the Icicle, above, President Franklin D. Roosevelt's ice yacht, from the Roosevelt Library in Hyde Park, N.Y. Sources: newyorktimes.com, iceboating.org, and Wikipedia.org Roosevelt’s.

-Michael Quick