When I say walking around Manhattan, I really mean around, for the most part anyway. This was supposed to be a 32 mile journey, but we ended up clocking over 35. Believe me, I felt every step of those extra, three miles. I’m not even sure what motivated my friend Jonas and I to embark on such a trek, but we’ve been talking about it for a couple years.

I had some history with this. My previous Manhattan circumnavigation attempt several years ago ended unceremoniously around West 86th. My shoes weren’t up to the task causing some painful blisters and I hobbled off to the subway. My walking partner at the time forged ahead only to succumb to a mysterious and sharp foot pain in Inwood Hill Park.

I mention this only because the truly wise man learns from the mistakes of others. While my blisters healed quickly, the other guy limped around for the better part of two months. Thus, my one stipulation for agreeing to this at all was “I’m going to stop at the first sign of any blisters or sharp pains.”

However, on this journey, the blisters didn’t really kick in until about 2/3 of the way in. By that point, the thought of having to retread those miles at some future point helped propel me to the end. For those last few miles, I was a bundle of misery. My usual, brisk pace was reduced to a kind of shuffle. All but the slowest of tourists were passing me. It wasn’t just my feet—though, they were the worst—my whole body was protesting with minor pain and major fatigue.

This will paint the picture of how beat I was: A quarter fell out of my pocket when I was retrieving my apartment keys. I began to bend down to pick it up and almost immediately said, “screw it, I don’t need 25 cents that badly”. At the time, I don’t think even a crispy dollar bill would have motivated me. A five? Maybe.

Who’s the wise man now? Certainly not me. But, we accomplished something As I write this, I’m happy to report that I’m back to 100%. The body is a remarkable thing, even this one.

So, to answer the inevitable “Would you do it again?” question: Maybe. But, I’m going to stop at the first sign of any blisters or sharp pains.

By the way, I’ve included a few observations and lessons learned below, in no particular order…

• We went clockwise, starting and ending around Fraunces Tavern. We thought this would provide some shade in both the morning and late afternoon (it did). This put us on the most challenging part at the end of a long day. However, to do it again, I’d go in the same direction to get that glorious shade for part of the day.
• The West side path is complete from The Battery, all the way to Inwood Hill Park, impressive. There are narrow and shared with cyclists. Some of the most narrow sections are right next to the West Side Highway. Obviously, these aren’t that much fun for anybody, be mindful.
• If you buy limonatas from people in the park, be prepared to negotiate a price up front, or pay a steep convenience markup.
• The section through Inwood Hill Park is amazing. It doesn’t feel like it’s in the city.
• Inwood and the East side of Washington Heights are a bit of a mixed bag. This is either on the street, or adjacent to or in city parks. We accidentally added some mileage here by going over to 9th avenue. Not a total loss since we did get to see the massive Kingsbridge Bus depot and Overhaul Shop.
• Getting back to our planned route, we walked by a roast pig truck on Academy & 201st Street. This was a big operation with a separate BBQ pit truck that held 5 or 6 pigs. They weren’t open yet, but they did give us a sample, which was delicious.
• At Dyckman Street, we went up into Highbridge Park rather than staying by the river. The park was nice, but added some elevation that we probably didn’t need on this particular day. I’d stick with the river next time.
• Navigating the East Side is somewhat challenging as there are a number of closures, both on the river path and the pedestrian bridges leading to and from it. This was even more frustrating because we hit it towards the end of our journey. Walking three-quarters of a mile only to find you have to walk back the same three-quarters of a mile is much more disheartening at mile 32 than mile 5.
• Take a light backpack with water and some food. Going into bodegas every few miles to stay hydrated is a pain, not to mention all the single use the plastic. There are numerous water fountains along with way for refills.
• Make sure you shoes and socks are up to the task!
• Plan your route and be ready to change it up given the conditions on the ground. Shorewalkers have an annotated map of the route around Manhattan that looks reasonably up to date.