I went to college in the East Village. Before that, I was mostly limited to exploring areas around my home and high school, both in Elmhurst, Queens. I commuted to school and often had time after class to explore the surrounding area. Having a location to serve as a destination helps and the various branches of the New York Public Library were my locations. The closest branch to school was the Ottendorfer Branch on Second Avenue. It's rather tiny and was a magnet for the homeless population in the neighborhood, especially in the winter. Further east there's the Tompkin Square Branch, right on the northern edge of Tompkin Square Park, where a major riot broke out between police and demonstrators in the 80's. I think I even ventured far south to the Hamilton Fish Market Branch on East Houston Street.
After college, most of the jobs I worked at were in midtown Manhattan, so I visited the Kips Bay Branch on Third Avenue, the Business Library at Madison and 34th Street (workstation with Internet connection, provide your own laptop, what a novelty!), the Mid-Manhattan Library, the Central Research Library with its two majestic stone lions, Donnell Center with its big collection of Vietnamese books, and many others in the midtown area. The best-looking library, in my opinion, must be the Jefferson Market Library on Sixth Avenue in the West Village. It used to be a courthouse, a jail, a marketplace, and its high tower was once used by the era's fire department for looking for fires. I wrote a Humanities paper on it in college and even got a decent grade for it, using fancy architectural terms and all.
One day I told my son I would take him visit a castle. That was the day I took him to the Jefferson Market Branch, where he picked out the DVD version of Chicka Chicka Boom Boom. In the photo, J was standing on the traffic triangle bordered by Greenwich, Sixth Avenue, and 9th Street.