Did it a couple years back during the spring on my own. It was quite the journey. I started at brooklyn bridge and went up the east side first. I remember the stretch along Harlem River Drive where you're sandwiched between the highway and the river being one of the most memorial parts of the walk, despite it being the most lonely section. Probably only saw like one or two people during that whole stretch but just being by yourself that whole time felt very serene in a way.