Shelter Island

Mashomack Nature Preserve
There is a nice nature preserve that would be a great place to see. It is part of the Nature Conservancy and comprises 1/3 of the island.
Kissing Rock
Also, there is a huge, well-known rock located at the end of Cresent Beach that was redecorated immediately after 9/11.

During the summer, once a week, the Perlman Music Camp, founded by world-known violinist Itzak Perlman, puts on a performance. The students are gifted young people and occasionally Itzak Perlman conducts the students.

The Ram's Head Inn
was the site of the Shelter Island Conference on the Foundations of Quantum Mechanics in 1947. Many famous physicists attended, including Oppenheimer and Feynman. A small plaque commemorates the event.