Walking the Length of Manhattan. I did this, solo, right before I moved out of NYC. Loved it. Will do it again someday.
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Or for a slightly longer walk around New York City: https://kottke.org/15/10/walking-every-block-in-nyc
In 2006, I lost my job. I lived and worked in Inwood, the northernmost tip. At that time, I played basketball at the McBurney YMCA at 14th street. My last day, I walked from the YMCA to my apartment. It wasn't the whole island, but I think roughly 7 miles. I sort of zig zagged as the traffic lights allowed but spent much of it along Broadway. I stumbled upon the diner from Seinfeld accidentally. I still look fondly on that walk and the outrageous amount of miles I walked during my 4 years there.
I should specify that Inwood is the northernmost tip of the island, not the borough!
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