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My Date With New York City

Updated: Dec 13

It started years ago as a brief encounter in the dark, but now Travel Write editor Warren Prentice wants a proper relationship with NYC and, as with all relationships, first impressions matter.



It is a dumb question, but I ask him anyway. “Do you ever get tired of seeing this amazing view all the time?” We are perched on the narrow viewing deck of the Empire State Building, 1000 feet above the gently humming streets of New York City, the nearby buildings lagged in the cotton wool curls of an 8am mist.


He straightens up from leaning on a rail, with as much dignity as is possible for an employee obliged to dress as a 1930’s doorman, pauses briefly, but long enough to look slightly pained, and says “Sure I do man. How do you feel about your job every day?” Like I said – a dumb question.


Visiting a city for the first time is like going on a date. Nothing is exactly like how you imagine it and there are always surprises, both good and bad. Most of all though, first impressions matter. I am visiting New York for the first time and we are both on our best behaviour.


There is nothing new to write about New York City, right? Well, how about that the locals are actually friendly and welcoming? New Yorkers, the fabled Kings and Queens of the sharp put down and the smart wise crack are not that fierce in real life. Empire State Building man played up to the stereotype, but he was alone and, in his defence, I was definitely asking for it.


So, first impression No.1? New Yorkers are as friendly as anywhere else and keen to share their love of their city with visitors, just as long as you don’t block the sidewalk with tourist crawl-walking, obviously.


I first saw New York in September 1993. It was magical. It was also 3am and I was on a train to Washington, struggling to sleep on a rock hard seat apparently designed by a diminutive sadist with a hatred for anybody over 5’ 4”. However, the battle to maintain the blood supply to my feet was spectacularly interrupted as, for a glorious minute, maybe two, the track briefly emerged from a tunnel and ran along the New Jersey shore.


Suddenly, as if I was watching on a yet-to-be-invented wide screen TV, there were the million twinkling lights of the Manhattan skyline. Soaring hundreds of feet into the sky, like a giant sparkling forest, they left a shimmering broken reflection in the otherwise black ribbon of the Hudson River. These were inanimate buildings yet they seemed alive. The whole scene was obviously real yet so strangely unreal. I had seen New York in films and books, but not like this. This was like nothing I had ever seen before.


The scale was jaw-dropping and I guess I probably was sat with my mouth open. As the train plunged back down into the subterranean darkness, I had the satisfaction of having seen the greatest city on Earth for the first time, and in dramatic style. The train rattled on South but I knew I would be returning very soon.


How do you define “very soon”? For some of us it means tomorrow, or next week, or maybe even next September? Time passed. In fact, a lot of time passed. For me and New York it would be another September, but 24 years later.


Family connections meant that for two decades New England was my US destination of choice. The wooded carpet of Vermont’s Green Mountains, the craggy wave-battered shores of Maine, neat Massachusetts college towns straight out of a Norman Rockwell painting, these were my American experience.


However, not having been to New York “properly” began to weigh on me a little. After all, even people who have never travelled anywhere else in America have gone to NYC, right? I had to confront the truth. I was a middle-aged "New York virgin" and it was finally time to pop my cherry.


My wife Karen and I exit the arrivals hall at JFK (I know that being accompanied by your actual partner stretches the "date" metaphor somewhat, but bear with me on this one). We are both excited about jumping into an iconic yellow cab for the journey into town.


However, the sleek long-bonneted 3 litre monster saloons of our childhood “Starsky and Hutch”-influenced memories are exactly that, just memories. First impression No.2 - New York taxis are disappointingly ordinary. In fact our cab closely resembles my Dad’s old 1980’s BT work van, minus the pile of tools and broken phones.


The journey into Manhattan is a long hot crawl along a packed Van Wyck Expressway (aptly named after one of NYC’s less go-getting mayors) followed by a brief teeth-chattering 60mph dash towards the midtown tunnel.


So far we could be anywhere in America, but, as we crest the last hill in Queens, the entirety of Manhattan dramatically swings into view. It looks like one of those ridiculously over-blown space stations that always feature in big budget sci-fi movies. This time I am seeing the city in daylight, and from the East, but it is still a mind-blowing view.


Dead ahead, their distinctive art deco lines clearly marking them out from their boxy glass and chrome neighbours, the Empire State and Chrysler buildings guard Midtown. To the left and South, the Brooklyn Bridge, Downtown and the mirrored behemoth that is 1 World Trade Center. To the right and North, the Queensboro bridge, Roosevelt Island and the well-heeled Upper East Side. Here is New York City, in two turns of the head. We have arrived.


When you pick a hotel in the dead centre of Manhattan, just a block away from the Empire State, what is the first thing you notice? First Impression No.3 – The buildings are a bit scary. This may seem a bizarre observation when visiting a city renowned for its many skyscrapers, but it’s a scale thing.


Other cities have tall buildings, but here tens of concrete and glass leviathans loom threateningly in every direction, blocking out the light and creating urban canyons that run arrow straight to unseen vanishing points. It is initially unsettling and it takes a while not to feel a tad queasy when looking up.


Then there is the noise. All big cities are loud, but New York transcends a simple word like noise. The decibels lurch into the red the moment you step out onto the street, with enough volume to require a new descriptor like “omni-loud”, “mega-din” or whatever else you can think of. Assuming you can hear yourself think, that is.


This place seems to have more car horns, pneumatic drills, and screaming fire trucks than anywhere else on Earth. More than any other city, New York never stands still. New buildings rise up all around as others disappear and the pace of constant renewal is relentless. First Impression No.4 – I am having to shout just to conduct a normal conversation.


The next morning we explore up Fifth Avenue, detouring to the Art Nouveau glory of Grand Central station, the smooth elegance of the Chrysler building, and the thumping inelegance of Trump Tower.


This morning though Fifth Avenue has a pantomime feel as we are passed by a group of moustachioed middle-aged men, all wearing matching tight lederhosen. It is a striking look. The “Sound of Music” vibe grows as a bunch of Oktoberfest barmaids cross the street. Then, outside St Patrick’s Cathedral, we are suddenly engulfed in Oompah music hell as the lederhosen guys, barmaids and a firefighters' brass band add themselves to a milling mass of OTT fancy dress chaos. It is like a flash event for Wagner fans.


This, it turns out, is German-American day when everyone dresses up and hangs out with some real Germans to celebrate Teutonic fraternity. It is an excellent reminder of NYC’s and the wider US’s melting pot history. If there is an equivalent British-American day, I imagine everybody wears Fred Perry and trackie bottoms.


At 59th Street, Grand Army Plaza and it’s deliciously tasteless golden statue of Civil War General Sherman, acts as the gate between the Midtown canyons and the glorious space and relative peace of Central Park. If any single place can be regarded as the heart and soul of NYC, then arguably it is here (although Times Square comes very close).


Central Park was designed in the mid-Nineteenth century, with more than a nod to the English stately home garden tradition of Brown and Repton. It has been Manhattan’s back garden ever since, despite occasional periods of neglect and under funding. Clever landscaping means new views open up at every turn. Intimate woods nestle tight to open greens and everywhere there is a huge variety of trees from across North America and beyond.

On this Saturday lunchtime the park is busy with New Yorkers indulging in just about every leisure activity possible on land, and a few on water too. There is a junior chess tournament by the boating lake. Cyclists, roller bladers and horse-drawn carriages vie for space on the meandering park roads. Sun lovers worship on Sheep Meadow and noisy Sea lions are the main attraction at the tiny zoo.


The park is long and relatively thin, but there is still plenty of room for everyone. Standing in the middle, it is just possible to spot buildings on the Eastern and Western flanks, but walking end to end will take you a couple of hours.


Central Park is important to Manhattan because there are so few other sizeable green spaces on the island. Bryant Park at 42nd St and Downtown’s Battery Park are relatively tiny by comparison. The other boroughs are slightly better served but, on Manhattan, Central Park is your main option if want more than a thin strip on which to cycle, skate, exercise your dog, recite your mantra, or just see more than four trees. First Impression No. 5 - I had no idea how lovely Central Park was. This is now my favourite place in New York.


It is 8am on Sunday morning and we take advantage of our hotel’s close proximity to ascend the Empire State Building, enjoy a slightly misty view and ask the staff stupid questions. The legendary queues just to queue are not evident this morning. So, top tip readers! Book your ticket online beforehand. Get there very early, or very late (it doesn’t shut until 2am).


The super smooth lift carries us 80 floors in barely a minute, before we swap into a smaller lift to the outside observation deck on the 86th floor. The lift change is necessitated by 1930’s elevator technology only being able to cope with an 80 floor maximum.


Shooting back down to ground level, and slightly wobbly-legged, we catch a bus downtown. On a traffic-free weekend morning it is just as fast as the subway and you get a better sense of changing neighbourhoods. It is a fun journey, but the best free trip in town has to be the Staten Island ferry. The 25 minute commuter voyage crosses New York harbour, with impressive views of Downtown Manhattan, Ellis Island, Brooklyn and, of course, the Statue of Liberty.


Liberty was a very grand present from France in the 1880’s, long before people started gifting each other small candles and saying “Thank You” with Garfield the Cat cards. Call me old-fashioned, but a giant green copper woman with a spikey hat, waving a torch? That is a proper present.

Liberty is most famous as a beacon of welcome for the mass influx of immigrants that made the USA what it has been for many decades, a symbol of hope and opportunity for all. In an era where a US President allegedly complains about immigrants from poorer countries in derogatory terms, Ms Liberty may have lost some of her welcoming sheen, but she is a powerful reminder of the good America can still do, when it wants to.


Staten Island bills itself as the forgotten borough of NYC, the Cinderella to ugly sisters Brooklyn, The Bronx, Queens and especially Manhattan. Locals regularly complain they are bottom of the pile when it comes to facilities and funding. Stepping out from the neat modern ferry terminal at St George, the island feels like it has more in common with suburban New Jersey than the hustle and bustle of the other boroughs, but this is not all bad.


It may be because it is Sunday morning, but Staten Island seems a peaceful, relaxed kind of place. We sit on a bench and look out at the harbour view and far-off Manhattan. Behind us is the gently understated and tasteful memorial to Staten Island’s 9/11 victims. It is so quiet that all I can hear are tiny waves lapping gently against the sea wall. NYC First Impression No. 6 – It is possible to find peace and quiet in this city, if you know where to look.


Returning to Manhattan on the ferry, we take a wander through delightful Battery Park. This oasis of green at the tip of Downtown was hit hard by Hurricane Sandy in 2012 but, following an ambitious restoration, is now a great place to take in an overview of the harbour from the other direction. Nothing sums up New York more than munching a hot dog lunch with the Statue of Liberty as distant company.


Monday morning comes and we set off to explore The High Line, a remarkable piece of urban renewal involving the leafy makeover of an old elevated railway line. The boardwalk weaves for just under two miles through Chelsea, at 30 feet above street level, showcasing unusual viewpoints of midtown, the Hudson and the harbour.


The contrast of the rusting rails with the shrubs, grass and small trees works well and it is certainly worth a visit, just don’t expect peace and solitude. The High Line is very popular with other tourists and the ever-present construction noise does not diminish any for being 30 feet higher.

We make our way over to Greenwich Village, once the home of Beat poets, folk musicians and assorted other bohemians, now a Chi-Chi centre of middle-class gentility and posh independent “boutiques”. Sandwiched between the concrete forests of Downtown and Midtown, and with its neat tree-lined streets of brownstones, this is a more human New York. The scale is toned down, the hustle is diminished and even the air seems lighter.

In a bookshop surrounded by houses that are now only affordable for business moguls and movie stars, I buy a history of New York. It tells me, somewhat ironically, that Greenwich Village, along with nearby Tribeca and the Lower East Side were the areas where the poorest immigrants first settled in the Nineteenth Century as the city rapidly expanded northwards. Even as late as the early 1970’s this part of town was an affordable option for many New Yorkers, but no more. These days, recent immigrants are more likely to be found across the East River in sprawling Queens.


We finish our trip with a brief wander through the East Village, a drug-blighted tourist no-go area in the Eighties but now, like nearly all of New York, safe and relatively crime free. Come here if you want to see classic early Twentieth Century apartment blocks, festooned with zig-zag black metal fire escapes, the kind Harold Lloyd dangled off in his silent movie stunt scenes. It is largely a residential area, unremarkable even, and perhaps therefore the perfect calm down after a few days of taking in superlatives.


Whilst people watching in Tompkins Park, I reflect on my first proper date with New York. In just a short visit, it is impossible to see, do and understand everything but, for me, this city is simultaneously life-affirming, puzzling, glamorous, scary, cool and ridiculously intense. First impression No.7 - I think I am in love with New York and I won’t be waiting another 24 years to see her again.

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