• Read the more recent comprehensive post, From Penn Station to New York Landmarks: Measuring Walking Distance and Time in Manhattan.
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Walking 20 blocks uptown or downtown in Manhattan is equivalent to one mile. An example then would be that a walk up 5th Ave. from 8th Street to 28th St. would be a mile and from 8th St. to 48th Street would be two miles. This comes in handy when assessing distances. A fast walk is a 15-minute mile, so if every single crosswalk light is in one's favor, then a walk from 8th St. to 48th. should take 30 minutes. It usually takes me closer to 40-45 minutes.
Rational measurement does not work for most of lower Manhattan. This is especially true for the West Village, a bohemian labyrinth. I have seen visitors, drunk on sugary cupcake frosting, walking the wrong direction on Bleecker Street. I just let them walk off their cupcakes.