The medal's obverse bears a galleon under full sail, facing half right. Around, YACHT · RACING · ASSOCIATION · OF · LONG · ISLAND · SOVND ☩
The reverse bears a wreath surrounding center field left empty for inscription.
The edge is marked BRONZE.
The Yacht Racing Association of Long Island Sound traces its roots back to a 1906 meeting of nine or ten avid sailors, including George Granberry, Harry Jackson, Dr. A.E. Black and J.W. Alker. They had gathered in the Hotel Astor's yachting room and came up with the idea of the Handicap Yacht Racing Class of Long Island Sound. From the humble beginnings of six boats competing on one class the association quickly grew to hundreds of boats racing in multiple divisions and classes.
While I could not track down a date for the first medal award I am fairly confident that medals were awarded early on in the association's racing history and have dated the medal in the 1900's. A much more abstract (and much less expensive) version of the medal is still awarded today.
The circular medal measures 77mm in diameter and was struck in bronze by Tiffany & Co. of New York.