508 Miles: introduction (9.18-9.25)

Walking Manhattan

Moving to New York is an agreement to compromise— being here is worth enough that you are willing to trade space, financial security, and ultimately any semblance of quiet.

Yet when you get here you trade the never-ending expanse of the city for a tiny neighborhood of established routines no larger than the options available to you in any midwestern strip mall. My greatest fear is leaving here without ever having known it at all.

I spent the last six years in Boston. A city that for every single one of its faults welcomed me into a never ending maze of streets and beautiful neighborhoods. It was a city I fell so deeply in love with that I walked every street three times over.

In my final days there, I paced through my last segments of my third big walk realizing that I would never know the city better than I did in that moment. Leaving has been a process of mourning: the slow forgetting of the esplanade on a summer evening, the quiet of Back Bay after a fresh snow, or the leaf covered streets of inner Cambridge.

Over the years I’ve written about my belief about the importance of walking. When you live in a city its easy to fast-forward your life until your life is a mirage of blurred memories. You become prone to filter every day into a series largely composed of high speed, out of body, moments in cars or trains interrupted only by postcard-worthy moments.

Walking forces you to break a city into its tiniest parts. Walking prevents you from fast-forwarding. Walking turns your brain off. Walking is a religious experience.

Over the next year or so, I’ll be walking Manhattan. Along the way, I’ll be making maps and images of the walks.

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Day 1: Sunday, September 18, 2022

7.34 miles. 83 degrees and sunny.

Starting in Gramercy Park before marching south down 2nd Ave, dead-ending into the horrible Manhattan Bridge onramp that in the summer heat feels somehow more hellish on foot than from your Uber, tracing West through Chinatown onto Canal Street, before heading North through an unusually chaotic Little Italy (Feast of the Saints and all that), getting lost in SoHo trying to find the new J.Crew Mens popup (excellent), before scrambling across Washington Square Park into the Village, falling in love with with a few vintage Jaguars, and then back East along the unusually stinky 11th Ave to Irving, and following Irving home to Gramercy Park. For a first day in the city, I couldn’t imagine a more perfect walk.

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Day 2: Monday, September 19, 2022

3.53 miles. 68 degrees and muggy.

Headed West from Gramercy Park along W 22nd past Cote (the best Martini in the world) before running into a set of men in immaculate suits excitedly sharing a saline inhaler, before hitting the river. Then headed home along W 20th passing the birthplace of Theodore Roosevelt and the Westside Rifle and Pistol range. The city is in the middle of two great rivers, but you’d never notice it. An incredibly strange experience after spending so long in Boston— a city defined by its river.

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Day 6: Fri, September 23, 2022

10.10 miles. 61 degrees and perfect.

Starting in Gramercy Park heading straight up Lexington past the world’s longest stretch of Veg Indian Restaurants before stumbling through the seven levels of finance and Hunter College’s strange and soviet campus, before the beautiful streets of the Upper East Side and a thousand custom suiting stores (Houndstooth seems the flavor of the season) turning West at 83rd to the Met, and then North to the reservoir, around the reservoir and back out onto 85th cutting one over to head South down Madison Ave deadending into Madison Square Park (home to the Edition who’s dramatically underrated lobby bar was a second home to me for many years), and tracing back to Gramercy to complete the loop.

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Day 7: Saturday, September 24, 2022

7.63 miles. 63 degrees and a perfect false fall.

Starting in Gramercy Park before heading North all the way up 3rd to 84th through some of the most unremarkable blocks in the city (save for the Bed Bath & Beyond Coffee shop concept), heading West on 84th street to Brodo (broth is more effective than nearly all other medicine), across the park circling around an oddly well armed security detail protecting a “social good festival” that blocked nearly path in the park, finally out of the park on W 81st, hopping up to 82nd, and finally north to John Koch antiques.

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Weekly Stats: 26.18 miles covered, 7 hours.

Progress: ~4% of Manhattan complete

Reflections: a low milage first week, with all the hectic social obligations of being new somewhere. New York is perfect in the fall, and every walk here is a blessing.