First Off – you asked about NYC and the responses so far have been focused on Manhattan Island. Brooklyn, Queens, The Bronx, and Staten Island (East New Jersey) all have their own random traditions and while they all have some grid areas they don’t follow the same logic as Manhattan.
As far as Manhattan-specific –
All of the responses so far apply *above* Houston Street – pronounced – How-stun, which if you Google Map is, is roughly the upper 9/10ths of Manhattan.
The bottom 1/10th of Manhattan is an irregular assembly of random roads and streets like any Colonial US historic district. There really is no method or pattern to learning those streets other than lived experience. This area in lower Manhattan that’s chaos includes such famous neighborhoods as the Financial District, SOHO, Little Italy, Chinatown, Greenwich Village, and the Lower East Side.
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