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Desperately Seeking Victory and a Good Time at the Pinstripe Bowl…in Gotham

As the Iowa Hawkeyes try to break an awful bowl game losing streak in New York City, how can you make a trip there a winner regardless of the outcome of the game?

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“One belongs to New York instantly, one belongs to it as much in five minutes as in five years.” - Tom Wolfe

My first real time spent in New York City was spent in a New York City that no longer exists. The New York City of before 9/11, most people who live or commute there will tell you, faded into the night of that tragic event. Nevertheless, my love affair with the greatest city on Earth was born in a version of itself that I believe still, on a spiritual level if nothing else, continues to exist. There is an ember of magnificence that continues to burn brightly beneath its latest veneer that makes this place every bit as bewitching and memorable as ever.

Years ago after serving twenty-something years in the United States Army my father retired started a new career in the civilian world working for an oil company whose headquarters was in NYC. I was a freshman at Iowa during his career transition and was excited to get “home” to see the new digs he and my mother had settled into that first Christmas break, in the bedroom community of Ho-Ho-Kus, New Jersey just outside NYC. But, really, what I was most eager to do was go explore the hallowed grounds of Holden Caulfield’s torturous effort to come-of-age, which was now 20 miles away.

Scarcely 24-hours after I’d arrived from Iowa City I was commuting alone into “The City,” as locals called it. It was a few days before Christmas when I arrived at Port Authority Bus Terminal in midtown, which, at the time, was maybe the most grotesque bus station in any civilized country. I got off the bus and was jarred hard into an alternative reality, one quite at odds with my newly acquired suburban home base or my idyllic college town residence. To exit the bus station I would have to weave through junkies, hookers, panhandlers, gangs, a potpourri of people with non-existent sanitary habits, all alongside perfectly coiffed men and women in handsome suits heading home from their executive toils. Sure, it might have served — at that moment — as the most democratic experience of my life, but it also was overwhelming to my logical senses. I trudged on trying to look unaffected.

My modest overarching goal was to see that damn Christmas tree at Rockefeller Center, the one that was likely taller than any building in Iowa City that they always showed on The Today Show and a zillion other news programs as a sign that Christmas has officially arrived, and to have some classic NYC pizza.

I was also hoping to maybe find a bar with a few college girls who, like me, were home for the holidays, and then to hopefully return home alive. I’d been given some advice by a new neighbor on how to get in, how to get around, and even what is and isn’t good pizza. Sadly, he provided zero advice on where might be a bar with college girls.

In those days there were no cell phones, or internet for that matter, so you had to explore using your sense of direction, some basic common sense, and more than a little bravery, not unlike how you’d try to survive if your car had broken down at twilight in the Sonoran Desert, all of which made for more than a few aimless walks with bad turns down bad alleyways, but also made New York City feel like a thrill ride at a theme park.

I got a subway map at the bus station and, for all intents and purposes, had the night of a lifetime. I did find a bar with college girls, by the way. That was surprisingly easy, and while my first foray was less literature-worthy than Holden’s, it felt, for a kid who’d never seriously been in NYC, every bit as dramatic. I met very interesting people, did things I’d never done, saw things I’d never seen, learned things I’d never thought I’d need to know, all in about 8 hours. By the time I was back home, ensconced in a bed with fresh sheets in my parent’s guest room (I’d lost my bedroom in the move), I was different. I’d changed and I had no interest in going back to the narrow frame of mind I had before. I’d been in the ultimate urban jungle, confronted my share of wildlife, and like a native American after a vision quest, I’d found at least one new purpose in life. And that is New York City. If you let it, and certainly if you want it to, it can serve as your passageway, your awakening. When I awoke the next morning I knew one day I’d move into The City, which I did years later and stayed for well over a decade.


This is a very biased New York City guide, built from my experiences, and reflecting my prejudices and as a result my advice will inevitably contrast or even be at odds, and maybe wildly so, with the experience of others around here who have also lived or visited New York City. (Which is fine and I hope the comments section is overflowing with alternative takes.) But bias is good sometimes. I had an English teacher once who upon reading a writing assignment of mine told me, “Never write the words ‘In my opinion…’ because of course it’s your goddamn opinion. You wrote it! It’s a given son.” And until the internet acronym “IMO” made its way — regrettably — into my online writing, I tried like hell to never say or write those three words after that scolding. So, this while this is obviously my advice on how to enjoy this incredible town, make no mistake, this is not the advice of a grizzled New Yorker. In fact, I’ve never tried to convince anyone that I am a New Yorker. Sure, I said for over a decade, “I’m from New York,” when I was traveling, because it was geographically true at that time, but it was not culturally true—and that is a distinction. There is a huge difference between living in New York City and being of New York City. My experience of New York, even today when I trudge in to see a doctor or meet a friend for dinner or take my daughter shopping or whatever draws me in, I go as an outsider, a visitor. I have never taken ownership of New York City and never wanted to. It was much more fun to be there as a perpetual tourist, a vacationer that lives on day after day on his vacation. As a result, I hope you will find what comes next as trustworthy and reasonable, and most of all, relatable.

Let’s go.


When one visits New York City one is advised to adopt the attitude of a private investigator. Give yourself an assignment, serve as your own client, if you will, and then set off to investigate with focus and emphasis. Why? Well, to me, and this is the most important thing I’ll write in this post: New York immense and overstimulating. If, in a moment of undisciplined curiosity, you stopped to explore most everything that was before you on the streets of New York City, you would:

  1. Get nothing worthwhile done
  2. Very, very likely spend your hard earned money and precious time at some of the most pedestrian versions of whatever it is you stopped at, ad hoc, to investigate
  3. Get ripped off, taken advantage of, and likely bamboozled

Here’s what I mean. You are most certainly going to walk by a cool looking bar or two or more, and think, “Let’s check this place out!” As if you are a perpetually hungry bushman looking into a dark cave to see what sort of meal may happen to be in there. It will feel daring and impulsive, and you’ll have engaged some level of audacity, which is one way to travel. You will go inside and it will be fine, maybe even upon first blush, spellbinding (“Look at all these gins!”), and you’ll probably have a perfectly good time — and yet that bar will be a dime a dozen in NYC and invest nearly no meaningful memories into your trip. If that bar is going to become, after all, the subconscious window dressing to your trip, it should be special (which means, either historical or truly distinctive). Yet, because you were flying by the seat of your pants, you ended up in a NYC bar that by NYC bar standards may as well have been a bar in Kenosha or Topeka or any number of “not a New York City” bars. That decision will have undermined the whole reason you decided to go to New York City in the first place, which should be to be bowled over (pardon my pun), and worst of all you’ll never know what could have been.

I have travelled widely, the results of a life spent in the military where I attended nine schools between kindergarten and high school. I was literally raised to roam around, introduce myself to strangers, and make a go of it. Some of the cities I’ve visited, especially in Europe, are perfectly suited to the ad hoc, fly-by-the-seat-of-your-pants ethos that many casual travelers prefer. But, I’m warning you that to do this is a waste of money and time in NYC. I feel so strongly about this that I’m inclined to tell you that if you must operate like this, then don’t come. Save your time and money. Spend your hard earned cabbage on a trip to Cancun or Montreal, which right now are fairly affordable trips (especially compared to one to NYC), and once you are there you can drop into whatever you like, on the fly, and it will all be mostly the same, and you’ll have made a reasonable choice, missed very little, and thus have had a great time.

Okay, that seems very strident. Can you have a good time freeballing a trip to NYC? I guess, because you will likely be with friends and it will be a “vacation.” Will it in any way approach what kind of experience you could’ve had? Unequivocally, no. Moreover, you will likely spend no less money or time operating this purposeless way. Make a plan, trust your plan, stick to your plan, and enjoy the sights along the way to arriving at your planned destinations. I guess what I am trying to say is that New York City requires some touristy control.

So, without further ado…here we go.

Let’s start with a bar, shall we?

MCSORLEY’S OLD ALE HOUSE - 15 East 7th Street (cross: 3rd Ave). It’s history. Not European-style history mind you, American history. In Europe there are probably well over a thousand bars older than McSorley’s. In America? Probably less than a dozen. Abe Lincoln quaffed a beer here after giving one of the most important speeches in American history at Cooper Union (right next door). Is that history enough for ya? You are not there for the beer, although you should have beer there. You are there for Americana. You are there to drink in the footsteps of some of the greatest writers, politicians, academics, criminals, musicians, you name it, to ever walk onto the rock that is Manhattan. And when you’re there, buy a hoodie. That’s what we do in the millennial age. Sure, it’s touristy as shit to buy a hoodie but it’s also a pretty cool hoodie. I had mine for 20 years before it gave way.

EMPLOYEES ONLY - 510 Hudson Street (cross: Christopher Street). This is not history. Well, it’s ersatz history (prohibition bar). Nevertheless, I like it because they know how to make a cocktail, and they make a few (I have a massive home bar and collect booze and cocktail recipes, which is to say I take this, as well as coffee, seriously). Honestly, there are a lot of these cocktail bars in NYC nowadays []. But, I have actually been to this one, and more than once or twice. If you are going to appropriate history you may as well go balls to the wall. They do. Sit at a round table, drop some quan, and act like you have a bodyguard with a Tommy Gun sitting in a Model T outside waiting patiently for you to finish. Oh, and it’s in a great neighborhood for exploring before or afterward, and, finally, if you have one too many and need to balance things out, the food is damn good.

You may have heard, NYC is ethnic.

You have to embrace this. You can get food from any of the cuisines of the world in NYC, a town with over 40,000 places to eat (10,000 open and 10,000 close, every year). Because there is just too much to see in a few days I recommend you take the most obviously touristy route on this and either go to Little Italy or Chinatown for some fun, or both. (I am in no way, with the following advice, telling anyone to privilege these suggestions over Indian, Turkish, Greek, Polish, or any other of your favorite ethnic cuisines here. In fact, if you have those tastes, embrace and explore them, please! The internet is your friend, and here [LINK] is a great resource for food evals. )

LOMBARDI’S PIZZA - 32 Spring Street (cross: Mott Street). This was the first pizzeria in America. So, they’ve been doing this a while. For my money, this is the best pepperoni pizza in NYC and it’s in Little Italy. I absolutely love it. You may not love it like I do, and if so, that’s fine and that is why the history is a nice complement. But, I have never taken anyone here who told me afterward they didn’t at least like it. It’s not tarted up pizza, which I like. They use a coal oven. They use fresh, homemade everything. The pepperoni is unlike any I’ve had before or since (super salty goodness). The tables are small. The bathroom is small. The interior is nothing special. There will be a wait. But, man, that pepperoni. If you go to Little Italy you gotta go here.

Afterward, walk around because that is really all there is to do outside of eating in Little Italy, and make no mistake, that is what NYC is all about — walking, so embrace it (wear proper footwear please). Besides, after the pizza you’ll need to walk around. But, eventually find your way into FERRARA BAKERY (195 Grand Street) and order a cannoli or, better yet, the hazelnut gelato, which is made in-house and is delicious [insert explanation on difference between gelato —more milk, less egg yolk, served warmer, more creamy — and ice cream].

Right next to, well surrounding actually, Little Italy is Chinatown. There are definitely more choices for eating in Chinatown, so I am just going to give you my two favorites. First up is WO HOP (17 Mott Street). It is in a basement, and it is very low key, and very much workers food. If you have been to China, that is the bulk of China, workers. But, I love it. There is nothing elegant or elitist about this place and it has all the classics. You will not leave hungry either. But, if you are looking for something with more culinary delicacy then I recommend my second choice, NOM WAH TEA PARLOR (13 Doyers Street). It is a dim sum place and you order using a paper checklist by checking your choices in classic dim sum fashion, which is so old skool cool it might be reason enough to go. I recommend you get a “bun,” some tea, and certainly the egg roll as a foundation to your order and then I recommend you over-order the rest so you can try as much as possible.

Also, while you are in the area, which you will also need to walk around to enjoy thoroughly, visit AJI ICHIBAN CANDY STORE (37 Mott Street) and check out all the Asian candies (definitely buy some Hi-Chews for the road). Great gifts for those who were too chincy to come to NYC with you.

Let me close by saying that I recommend you visit Little Italy and/or Chinatown during the daytime and eat lunch while you are there. You will want to take advantage of the daylight to see the sights.

Wintertime is the right time.

Ice skating within the confines of a major urban city is not unique, nor is ice skating in a park among the trees. But, to ice skate with both of the above, and in the shadow of 75 and 90 story buildings? That is incredibly unique and that is what it’s like to ice skate at WOLLMAN RINK in Central Park.

Now, listen to me carefully. If there is any snow in the forecast when you are in NYC, then that is the day to go to Wollman. It is also critical that you go at or after sunset. In the age of the selfie there is no more romantic, no more New York-y selfie than ice skating at Wollman Rink during snowfall surrounded by trees and behind them, iconic buildings scraping the skyline of NYC. They rent skates of course and serve booze, and if you are in a group, all the better. An hour or so is all you will need to punch this ticket, and you will remember it forever if the weather cooperates. One last thing: they take CASH ONLY!

So you like art.

Well, so do I. Of course I could recommend either THE WHITNEY or MOMA.

Both showcase great modern art. The Whitney (99 Gansevoort Street) will be less crowded, focuses more on American modern art, and is downtown. Moma (11 West 53rd Street) focuses more on international modern art and is uptown, in a better building. Both are fabulous and well worth taking the time. But, I’m going to recommend THE GUGGENHEIM MUSEUM (1071 Fifth Avenue) instead, which is in a landmark NYC building designed by Frank Lloyd Wright. It will not have “better” art on display than either The Whitney or MOMA, but it will display it more uniquely and I believe more memorably.


I am very much a hardliner on this one. You must go to the EMPIRE STATE BUILDING (350 fifth Avenue). There are other very tall buildings that you could choose to visit to see NYC from the air, but this building here is fucking incredible history. King Kong did not climb the Chrysler Building. As a matter of cultural history, I refuse to entertain any other building as an option. The views are astonishing. It will be busy UNLESS you go super early. The question of, “Do I go during the day or at night?” is also an easy one for me: daytime. There is no better way to see the incredible complexity of NYC’s urban design than from the Empire State Building. I have been to the top of this beauty no fewer than 20 times. I love it.

Give me your tired, your poor, your huddled masses yearning to breathe free.

Battery Park is the launching point for your visit to perhaps the most emotional experience New York City has to offer. When I first visited ELLIS ISLAND I was a grown man, with a small child and a wife, I was reflective and maybe that explains it. Nevertheless, I expected to go through the touristy paces and see the great statue and some names on tablets and for that to be it. Instead, the entire ride out on the boat I was overwhelmed with thoughts of what it must have been like to arrive in America from elsewhere, perhaps not speaking English, perhaps having no relatives to fall back on for support, and making a go of it. Once I stepped foot on Ellis Island, I lost it. You may or may not have a similar response, but I cannot think of a more important American experience, and I have been to Plymouth Rock, Jamestown and Colonial Williamsburg and throughout Philadelphia (Liberty Bell) and Boston (Faneuil Hall). Though the line for the ferry from Battery Park is long, if you get there early, you can avoid most of it. (Come late and I promise that you’ll have to wait a few hours, even in shitty weather.) The STATUE OF LIBERTY is shocking to see up close (for me I was awestruck by the size given its dedication date of 1886), but the real star of this experience is Ellis Island, where you will learn about the immigrant experience and get a sense of the people who helped build NYC. Use this info guide/map to get to the boat.


Must see. And, I would loop it in with Statue/Ellis Island visit. I recommend going after your trip to Ellis Island. You might ask why don’t I see this as the most emotional tourist experience. It’s a fair question and it might very well overwhelm you. I was walking to work when the first tower was hit. I thought it was a Cessna airplane, and so I continued on my way toward the train before being stopped by a crowd around the corner that understood this to be much more serious than some light aircraft accident. What happened over the next week has become a blur to me, and maybe I’m numb to it all now. I was fortunate not to lose any friends, but nearly all my friends lost someone. The one thing about this experience that always stands out to me is this: The silence. I have been three times and passed by the general area several times beyond that, and it’s always so very quiet. Please try to see it.


Can you visit NYC and ignore Time Square? Yes. Should you? This is not really an interesting debate. This is one of the most photographed areas of New York, so you probably should swing by. Will it impress you? Not really. I mean, the first time I saw it I was struck by the signage, the advertising, the lights (best at night) but over the years I have chosen not to take visitors here and some have gone without me and some ignored it. I don’t think it is required, but, again, if you can fit it in, go.

Key piece of advice: Do NOT eat donkey sauce or the food at any of the restaurants for any meal near Times Square. Trust me on this one. [EVIDENTIARY: The greatest Times Square or any restaurant review ever: LINK]


No architectural structure in NYC affects me more positively than Grand Central Terminal. My first few years living in NYC I would literally build evenings around being in the main concourse, at the now closed Grand Central Terminal Bar Pub that looked over the main terminal. I’d order a dirty Ketel One martini on the rocks with olives and a shrimp cocktail and then sit back and watch. I usually had to be pressured to leave. Rush hour was the best time to be there, and it is one of the most intensely NYC things one can do. While the bar no longer exists, the experience nevertheless remains and is required. Nowadays Grand Central has a vibrant life beyond mundane travel. There is first rate shopping, dining, and events. It is a photo op waiting to happen. I certainly recommend you eat something when you are there. If you like oysters, then The Oyster Bar downstairs is a good choice. Maybe make it a lunch stop during your travels? But, first, take it all in upstairs and as you watch the humanity flow across the floor just take in the poetry of it all.


The easiest way to knock down site visits is to buy the NYC EXPLORER PASS [LINK]. I recommend a “4-Choices” pass for $110. The pass is good for 30-days, helps you to avoid lines and does not require you to make any definitive decisions as to which sites you will use it on. I recommend you use it for:

  1. Empire State Building
  2. Statue of Liberty/Ellis Island
  3. 9/11 Memorial and Museum
  4. Circle Line OR Hop-on, Hop-off Bus

The Circle Line is a cruise around NYC, and I highly recommend it. But, if you are taking the ferry to Ellis Island you can miss the Circle Line and focus instead on the Hop-on, Hop-off Bus tour instead. Both will give you a great view of NYC, even in cold weather, but the ferry ride to Ellis Island will scratch the “from the sea” view of NYC for you. If you choose the bus then try to do this on your first day, then you can get off and back on at several of the sites I recommend above from the bus.


I am assuming you will have 4 days or so, which forces your hand. But, if you have more time or have been to NYC before and seen some of the sights listed above, here are some other fun and rewarding NYC things to consider (in no particular order):

  • Walk the Brooklyn Bridge - the Brooklyn Bridge offers an easy 25-minute walk into Brooklyn and the waterfront park on the other side. Stopping to take photos along the way will make the walk about 40 minutes. It is an architectural marvel.
  • Rockefeller Center - Wander around Rockefeller Center to see the Christmas tree, where they film The Today Show, shop, snack, and take the elevator to the “Top of the Rock” for another bird’s-eye view of the city.
  • Broadway Show - It’s not cheap but if this is your thing, do it. I have seen Hamilton, Book of Mormon and Dear Evan Hansen, and loved them all. But Broadway is much more than the big ($$$) ticket events, which these three most assuredly are. It’s another of a handful of quintessentially NYC things one can do. Come From Away is next on my list but discounted tickets are all over the internet. Buy in advance if you can, to allow you to better plan around the show. Again, do not eat food near this area!
  • Lower East Side Tenement Museum - This underrated museum showcases former tenement apartments on the Lower East Side. You’ll learn how immigrants lived during the late 1800s and early 1900s as they tried to make it in America. A great add-on is a side trip to Katz’s Deli, the best deli in NYC (order the pastrami).
  • The Doughnut Plant - Have a doughnut at one of the DP locations in the city. I recommend the Creme Brulee Doughnut.
  • Flatiron Building - take a few minutes to see and marvel at this iconic, unique structure. Then walk 5 minutes south to get arguably the best hot chocolate in NYC at The City Bakery (3 West 18th Street).
  • NYC Subway - I am always surprised by the number of tourists that never take the subway. Download the map app and ride this puppy. For nearly every location to which you will go, and especially to get to Yankee Stadium, you are best advised to take the subway.
  • St. Patrick's Cathedral - must see for the Catholics or cathedral buffs in the house.
  • New York Public Library (Stephen A. Schwarzman Building) - greatest library in the world. Pick up an audio tour device from the visitor’s desk in Astor Hall and learn something.
  • Caroline’s Comedy Club - one of the most reliable comedy clubs in a city with a ton of ‘em. I once did a 5-minute set here. Not lying. I bombed. My one joke that got an earnest laugh was about Robin Byrd, an old porn star who used to have a TV show on cable access interviewing strippers coming into town to perform, forecasting the weather on the Weather Channel (the two channels were once side-by-side on NYC cable).

Well, there you have it. Of course there is so, so, so much more you can and many of you will do. But this should get your juices flowing for the planning phase of your visit. Have a great trip!