I like doing open water races where national landmarks or locations dear to my heart are involved. For instance, I learned how to surf at Manhattan Beach so I like to do the Dwight Crum Pier to Pier race in August. I have always been fascinated with Alcatraz and had to experience what it would be like to swim from it to the city so I do the Alcatraz Sharkfest each year.
Randy sent me some info regarding some nifty open water races in New York City area that are landmark centric. Swims include:
Brooklyn Bridge Swim: [Link]
The Lady Liberty Swim: [Link]
The Governors Island Swim: [Link]
They are even more New York City swims here at the Manhattan Island Foundation: [Link]