Ran the perimeter of Manhattan, starting at 34th street and going north first/clockwise. I picked the starting point primarily out convenience, but I would recommend finishing the course on the West Side Highway since watching the sunset is such a treat during those final miles.
It was rainy on and off the entire day with torrential downpours at times (Got splashed by like 4 cars passing by…would not recommend.). Parts of the intended route were closed, so I had to improvise, especially along the East River. After the stretch along 1st Ave past the United Nations headquarters, the route takes you back to the water around 37th St, but much of the promenade is closed between there and Pier 17. The running path in East River park is under construction, so I had to backtrack there and ran on the sidewalk along FDR. Once you hit the Manhattan Bridge, there is a shared running+bike path under FDR that will take you past Pier 17 (with lovely views of the Brooklyn Bridge and downtown BK). This path then takes you along Battery Park where I took a route closer to the water so I could see both the tippy top and very bottom of Manhattan. From there, you’re on the West Side Highway for the home stretch, which I aligned with the sunset.
I ran alone the entire route and carried my own food. I refilled water at public water fountains (namely at Swindler Cove, Robert Moses Playground, and East River Park). In the stretch between Swindler Park and East River Park, there are few public water fountains- I happened on Robert Moses by accident.
All in all, it was a challenging but rewarding tour of the city- I feel I can really say I’m a New Yorker now :)