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Walking A City From Top To Bottom Offers A Moveable Feast

Urban Exploring

This combination of photos shows shows the grounds for Northwestern Univesity, left, cookies decorated with Chicago Cubs and White Sox sports logos displayed at Bennison’s Bakery in Evanston, Ill., center, and a highrise building on Lake Michigan in Chicago during a 12-mile walk through Chicago.

NEW YORK — We still had a few miles to go when the fatigue of being on the march all day started to settle in. Mathematically, we knew we could cover enough ground to finish our route by dinnertime, but we had to keep up the pace.

Our focus changed from enjoying the scenery to putting one foot in front of the other until we reached our finish line: the boardwalk at Brooklyn’s Coney Island. An ice cream sandwich at sunset was a well-deserved reward after walking about 12 miles from the northern tip of Brooklyn, in Greenpoint, down to its southern shore on the Atlantic.

While many people might lace up their hiking boots to spend a day in the woods, I’m a city girl and am more inclined to urban hiking.

My husband, John Tebeau, and I are fans of exploring cities on foot. We like to spend a day stopping in one place for a glass of wine, then another for a snack, turning a walk into a moveable feast. We can quickly get a feel for a neighborhood and its denizens while we walk and sit, walk and sit, walk and sit.

The opportunity to connect with a place on a human scale — asking a retail clerk or barista where we should stop next — feels like adventure fused with socializing.

This 2019 image shows the Coney Island boardwalk at sunset after a 12 mile walk from the northern tip of Brooklyn, in Greenpoint, down to its southern shore on the Atlantic.

Back in 2019, we walked the length of Brooklyn. We took the NYC Ferry up the East River to Greenpoint for a fortifying breakfast of doughnuts and coffee at the legendary Peter Pan to kick things off. Then we ambled on to a few spots for snacks and cocktails, and finally landed for dinner at Ruby’s, a beloved Coney Island bar.

In 2020, we tackled a slightly longer, 13-mile walk down the full length of Manhattan, starting at the tiny northern nub across Spuyten Duyvil Creek. Making stops was more challenging then, with many restaurants and bars not allowing people inside because of COVID-19, so we had to get more creative, especially about finding bathrooms. But after coffee on some church steps, live jazz in Central Park and my favorite New York pizza enjoyed al fresco at Arturo’s, we made it to the southern end of Wall Street.

We had moved to New York in 2006 and spent untold hours exploring all five boroughs. (John wrote and illustrated a book in 2018, “Bars, Taverns and Dives New Yorkers Love.”) But these walks still took us through parts of the city we didn’t know well, and showed us how one neighborhood gives way to the next.

Our most recent trek was part of a vacation this year in Chicago. We began by taking the train north to Evanston, home of Northwestern University, and then meandered down into Chicago. As the crow flies, our final destination in the Andersonville neighborhood was only 5 miles, but we zigzagged east to Lake Michigan and then back inland, ultimately doing nearly 30,000 steps according to John’s iPhone. That’s about 12 miles.

At a pace of about 20 minutes per mile, 12 miles is four hours of walking.

This combination of photos shows John Tebeau smoking a cigar outside of Cigars by Amadiz on Broadway, left, Tebeau in Times Square, center, and seated in front of a pizza at Arturo’s Coal Oven Pizza after walking the length of Manhattan in 2020. AP Photos

That felt easily doable when John first proposed what we call super walks. We live a pedestrian lifestyle in New York and have a walking routine. We go for a morning walk shortly after we wake up, then an evening walk after dinner.

But I overestimated how much those short daily walks would prepare me for all-day treks.

Walking for several hours, even with breaks, made my feet sweaty and swollen inside waterproof hiking shoes on our Manhattan walk. My sock seams rubbed my toes raw. Wearing sport sandals for our Chicago walk was mostly an improvement, but still I got a big blister.

Many long walkers advocate traveling light, but I was pretty happy to have bandages in my purse. As the Scout motto says: “Be prepared.”

Wayne Curtis, who was editor of American Hiker magazine and a contributing editor to Backpacker before becoming a cocktail writer, helped inspire our approach to daylong city walks. He noted that the best cities for long walks are those old enough to have been designed for humans, not cars. That means they have sidewalks right outside businesses, rather than strip malls with massive parking lots.

Curtis took urban walks while researching and writing a book, “The Last Great Walk: The True Story of a 1909 Walk From New York to San Francisco and Why It Matters Today” (Rodale).

“When backpacking, I learned to think ahead as to where I would next rest and recuperate, such as a ledge with a view, or along a nice brook. In cities, it’s the same, although these shady spots are called ‘bars,'” Curtis wrote for the drinks website Punch.

“A bar trek is a hybrid of James Joyce’s epic wandering and John Cheever’s pool marathon. I can traverse a city from watering hole to watering hole, from a stale-beer-smelling dive to a marble-and-brass hotel bar, down into valleys and up on to the peaks. At the end of the day, I view the city as more three-dimensional. I know where I am.”

Curtis likes to take his walks without a firm plan, perhaps having a few places in mind but no attachment to getting to them. If he hews too closely to an itinerary, he says, he becomes focused on checking off stops instead of actually engaging with the experience.

A fan of history, he leaves room for unexpected discoveries and solving mysteries. For example, when he walked across Louisville, Kentucky, he was struck by an especially beautiful park. He asked around and learned it had been designed by landscape architect extraordinaire Frederick Law Olmsted.

John’s long walking goes back decades. He has fond memories of walking with his college roommate to every place they knew of that sold egg rolls in Ann Arbor, Michigan, all in one day.

Even though our pace is leisurely and our approach far from athletic, a dozen miles is still about a half marathon. So it’s wise to take a cue from marathon runners and choose proper equipment like moisture-wicking socks and anti-friction gel. And soak in an Epsom salt bath afterward.

Unlike running a marathon, however, you can change the route of a super walk and adjust the distance as you wish.

“It’s really hard to make mistakes,” Curtis said.

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