Profiled here are fifty classic symbols of this extraordinary city, revealing little-known facts, longtime secrets, and historical legends.

Jonathan Scheff is a writer, photographer, and teacher. He lived in Brookline, Massachusetts, until he was eighteen years old; after that, he spent his time exploring the rest of the world. In 2010, he retired a pair of sandals that had walked in over twenty countries. He lives in New York City with his dog, Loki.