A while ago I was in some bike store and saw a flyer for the Five Boro Bike Tour, 42 miles through the five boroughs of New York City. Interesting idea, the cost wasn’t too bad (about $50), and sounded pretty unique to be able to bike through NYC’s biggest streets without the threat of being mowed over by a car or bus.

Then it started raining. At first it was a light drizzle biking through the streets of Manhattan, up past Radio City Music Hall, through Central park, and up through Harlem. At this point I still pretty comfortable and warm, Under Armour compression shirt, bike shirt, and bike shorts. There were little pit stops where water, bananas and port-a-potties were stationed. Over the river, and through the woods, mostly through the rain, we made it through. The whole time, my Garmin Edge 305 Bike GPS was having trouble keeping track of where it is, I suspect because of the overcast skies. According to the GPS, at the 25th mile, my socks went from a little damp to soaked. At this point I went from ‘Hey, this is cool biking over the Brooklyn Bridge’ to ‘My feet weigh a ton, and at this point, I hope I am not sick when I finish this thing.’ Making our way finally to Staten Island and to the Staten Island Ferry, several hours later I was cold, soaked, and ready to get out of those bike clothes. Hat tip to the Ritz Carlton Battery Park for your lobby bathroom, I was able to change into dry clothes there. There prime location to where the Staten Island Ferry left off made for a quick change and getaway back to Boston.

Overall the ride wasn’t very difficult. The 42 miles might sound daunting to most people, but there were a significant number of young kids, and parents pulling kids in carriages. It made me think that this ride could be done by most people in decent physical shape.

Yeah, I complained a lot during the ride, but it was a good time. I think given the weather and a few below suggestions, the ride could have been a lot more enjoyable.


None the less, I’ll still consider doing the ride again next year. The low cost makes me less apprehensive to calling it off that morning if the weather does not look welcoming. And who else could say that they were able to ride over some of NYC’s most famous bridges without the fear of death.