The Gilded Age, Grand Mansions and More: NYC History With Keith Taillon

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The Gilded Age, Grand Mansions and More: NYC History With Keith Taillon

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The history aficionado gives us the low-down on notable New York sites, his personal favorite spots, and what to expect from a KeithYorkCity tour.

Furloughed and ultimately laid off during the COVID-19 pandemic lockdown, former Ralph Lauren executive assistant Keith Taillon decided to keep busy—and sane—by walking every single block in NYC, from Marble Hill in the Bronx to South Street. In the process, Taillon also indulged his deep love for history, research, and storytelling, sharing much of what he discovered on his Instagram—and come June 2021, decided to try his hand (legs, rather) at giving a guided walking tour.

KeithYorkCity was born, and since then it’s “snowballed into a career,” the longtime Harlem resident and historian shares, with almost a dozen group tours and routes including a Gilded Age-themed offering centered around some of the sites and era depicted in HBO’s hit 2022 The Gilded Age series starring Christine Baranski, Carrie Coon, Cynthia Nixon and Morgan Spector. He’s also added a sequel tour to the line-up, “Gilded Age: New Money,” which commences in Murray Hill where Mrs. Astor lived, discusses the grand Vanderbilt mansions lost to time and other prominent (and familiar) NYC families.

Taillon, who was born upstate in Plattsburgh and earned a BA in History and Masters in Urban Planning, also puts together customized private tours (public groups typically cost $150 per person with a max of 10 participants, and private bookings between $500-900 for up to 8). His Instagram is filled with historic images of people, places, and important dates, and intensely researched, fascinating tales. 

In his Grandlife interview, Taillon shared the story behind his tours, what separates KeithYorkCity from competitors, his personal favorite spots and neighborhoods, attractions to not sleep on today, and his whopping 14-mile “Broadway Walk” itinerary.

The Gilded Age, Grand Mansions and More: NYC History With Keith Taillon
Keith Taillon conducting a tour in New York. Photography by Clinton Nguyen

First, what do you love most about your home base of Upper Central Harlem?

Keith Taillon: It feels very neighborhoody. I’m maybe 30 minutes from midtown or 35 from the west village and it feels a world away. It can be very quiet, a lot of single-family homes that they’ve lived in for generations so it feels very established and homey. Most of my time living in NYC has been in this one-square-mile radius.

Was there a specific walking tour experience that inspired you to do this yourself?

KT: Sort of. I dabbled in the idea during grad school at Hunter College for urban planning. For at least one class assignment they sent us on a tour of the Financial District. I won’t name names, but it was a very bad tour. So it was in the back of my mind that I could do better, but it wasn’t a reality until the pandemic hit and I lost my desk job and went all in on history, and through Instagram people started asking if I did tours and that’s what really sparked me to look into what it actually meant to become a tour guide and that process.

What did you want KYC to offer that was missing from other tours? 

KT: I’ve taken some decent walking tours, but I’ve always left wanting more. There’s ample space in the tourist universe for the kind of tour guide who just points to landmarks and says, ‘this is this,’ but my brain always hungered for something deeper. I’m constantly asking ‘why?’ when looking around cities. It’s difficult to find a guide who is willing or able or plugged in enough to unpack a place the way I want it unpacked. So I try to do that for my guests.

What are some misconceptions about walking tours?

KT: I think an obvious misconception is that walking tours are only for tourists. The fact is more than 50 percent of my guests are New Yorkers, who were either born and raised here or lived here for a substantial amount of time. They come to gain a better perspective of the city they take for granted, and buildings they passed by every day for 15-20 years they suddenly understand why it’s where it is, the way it looks, etc. So there’s a lot to be gained for locals taking a high-quality tour of their own home.

 

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A post shared by Keith Taillon (@keithyorkcity)

What’s your bestselling tour to date?

KT: Definitely Gilded Age, which covers the entire development of the city in the century between the 1820s and 1920s by walking from Washington Square up to midtown, about 34th street.

Was it popular even before the 2022 HBO series aired?

KT: Yes. I think the name is exciting and alluring, but especially since the HBO series came out sales have been constant. That route is sold out now through most of the Fall. 

Have any members of the show’s cast joined or inquired, like Christine Baranski who, I understand, has an apartment on the Upper East Side?

KT: Christine has not, I would be thrilled if she did, but I’ve talked to a number of the show’s cast and crew through Instagram. A lot of them follow me and my recaps of their episodes as they air.

Let’s manifest! Who would you love to join a tour or has already? Name drop, please!

KT: One actress who was incredibly kind and nice came on two of my tours, Keisha Castle-Hughes. She was nominated for an Oscar for 2002’s Whale Rider and has been in a Star Wars movie and Game of Thrones. She followed me on Insta, signed up for a couple of tours earlier this year, and brought friends. She couldn’t have been nicer.

What’s the most eclectic or unusual private tour you’ve ever been asked for or put together?

KT: In the beginning, I almost exclusively did custom tours and asked people what they wanted to see before I settled on set routes. In my first year, a couple asked for a spooky tour of places where murders happened and cemeteries and burials were. That was fun to put together and I’ve thought about rehashing it for Halloween. On several occasions, people have asked for routes based on their family history. They’ll send me their ancestry.com information and I’ll piece together where people lived and what they would have experienced, so half about their family and what the city would have been like when they lived there. The times I’ve done that have been rewarding for me and meant a lot for them.

What about LGBTQ-themed?

KT: I’ve done that on request a couple of times for some companies on Pride Month. I do include a lot of LGBTQ history on my general Greenwich Village tour, we start out with colonial history and pivot when we get to Julius bar to talk about the 1966 “sip-in,” the 1969 Stonewall riots, the 1970 raid and arrests at the Snake Pit bar, and the 1980s AIDS epidemic as well. 

 

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A post shared by Keith Taillon (@keithyorkcity)

History and your home base of Harlem aside, which neighborhood do you most love to hang out in and soak up the atmosphere?

KT: Really depends on mood and weather. If I venture out of Harlem I most enjoy walking around the Chelsea Madison Square area. If I need to go shopping, there are lots of great shops and bakeries scattered between the Meatpacking District, Chelsea and Madison Square. I like to get lunch at S&P Lunch near the Flatiron building, and right around the corner Dough Donuts and Fabrique Bakery. I love the coffee shop in the lobby of the Fotografiska Photography Museum on Park Avenue. A very chill place to grab a coffee, have a meeting or just sit and catch your thoughts or read a book.

What are the most underrated attractions or spaces in NYC right now? Just to start us off, how about The Cloisters?

KT: I think part of the charm of going to the Cloisters is it feels a little special, like you’re in the know, and it’s a bit of a journey. Even living uptown, you’ve got to ride the A subway line all the way up, take an elevator, and walk through the park. Anything where you feel you’ve got to earn the experience is special. And I don’t want to ruin anything by opening the floodgates to tourism, but getting out of NYC and Brooklyn to the kind of dense, vital, lesser-known areas like any neighborhood along the 7 train line, that corridor of amazing food out to Flushing, Queens, Sunset Park and Industry City in Brooklyn, Little Italy in the Bronx. These neighborhoods give you a much better idea of how New Yorkers actually live, rather than the shrink-wrapped versions in tourist-packed districts.

Do you like when parts of the city or buildings get redeveloped or repurposed, or are you mournful?

KT: I tend to be mournful as a historian because it’s hard to redevelop without damaging some semblance of what once was. I also try not to be too much of a “NIMBY.” I understand part of New York’s charm, allure and vitality is it’s constantly being redeveloped, I just wish it was more thoughtful sometimes, whether that be respecting a community that already lives in a place, pretending a neighborhood is just empty when there’s an underprivileged community actually living there and being forced out, or if it’s architectural. In underserved, non-white neighborhoods there’s a dearth of historic preservation protections, so when redeveloped buildings, and locations that may serve an important historic purpose in the larger story of New York, get wiped off the map, it’s without anybody even realizing how important they were. But I also feel like if [redevelopment] serves some kind of a greater purpose, like to remove Madison Square Garden to build a proper new Penn Station and all that comes with that, that might be a net gain for the future, but like many New Yorkers I’ve learned to be pessimistic because I don’t feel development corporations in general really care about the quality of life on the streets or the future 100 years hence and that makes me sad and mournful.

How do you feel about the new Moynihan Train Station?

KT: It’s imperfect but a huge improvement [over the old Amtrak Penn station across the street]. There’s a second atrium upstairs that isn’t used for anything yet, and I wish they would put some benches and a schedule clock up to make it a proper waiting room. The ground-level waiting room now is just silly: way too small, overcrowded, and this big grand train hall constantly has people sitting all over on the floor with their suitcases because they’re not serving the needs of the traveling public, which is what that building is supposed to be. But it’s still a huge step up, and I find that I and a lot of friends purposely take Amtrak and trains out of Moynihan now than we did Penn because it’s a more pleasant experience.

How do you think history will look back at the massive Hudson Yards and Vessel?

KT: A lot of that will depend on how it adapts after the first round of leases ends. I feel like, similar to what we saw happen on Bleeker Street and the Meatpacking District when these zones become really hot and ‘new,’ a lot of high-end luxury companies come in and sign a lease for a number of years, but usually, the profit margins never measure up to those expectations and they leave after the lease expires. We’re kind of seeing that happen with the Westfield Mall under the WTC right now. So for a historical comparison, Hudson Yards is somewhat comparable to Rockefeller Center when it was first developed. A lot of things changed in the first five or ten years. The sunken concourse was supposed to be a shopping mall, but that wasn’t very profitable so it had to be reinvented as a skating rink and dining concourse. I’m curious to see how Hudson Yards will change in ten years, and that will determine a lot of how it’s looked back on, but from a general architectural perspective, it’s not going to be fondly or kindly. The thing that drives me most crazy about it is they purposely designed it to turn its back on 10th or 11th Avenue. You can enter the mall from the corners and there’s a Sweetgreen salad there, but otherwise, it’s a big blank wall with freight entrances carved in, which essentially closes the whole complex off to the street which is antithetical to the way New Yorkers tend to function. So unless tourists really latch on and give it the romantic spin other older places have, I don’t think it’s ever going to live up to what Rockefeller Center or Grand Central have gained with age.

 

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A post shared by Keith Taillon (@keithyorkcity)

As far as the future of KeithYorkCity, are there any new neighborhoods, themes or routes in the works?

KT: I would like an East Village-LES-Chinatown-Two Bridges tour, but I’ve been hesitant because there are so many really amazing groups already doing tours there, like the Tenement Museum, Big Onion, and Bowery Boys tours. I always want to make sure I’m offering something new, so I’ve been mentally mushing that together lately and hope in the next year or two I can get something out there. Also a Soho-Tribeca tour. I’ve done them as private one-offs, but I’d like to formalize something I can offer to the general public soon.

You do an epic seven-plus-hour, 14-mile tour that stretches from NYC’s top to bottom. How to best approach that one if not a seasoned hiker or seasoned The Amazing Race contestant?

KT: I don’t normally offer that tour, but it’s going to be a New Year’s special and will go from Marble Hill to the Battery. We’ll see how it goes. I’ve only actually done it by myself, although I did something similar with another influencer friend who invited people to join her on a walk down, and people hopped in and out here and there. I don’t expect anyone who signed up so far to drop out, they’re a lot of my loyal regular customers. We’ll be OK.

I’d still love to see that as a reality show with a prize.

KT: I expect we all make it, but we’ll see.

Will people romanticize this era of NYC in the future, even with Chik-Fil-A locations popping up on every block?

KT: I think so. In certain ways, and we’re not entirely ready to visualize them yet, I think we’re living through a golden age when it comes to the arts when you think of theater and performance arts and the revitalization of concert venues like Kings Theatre in Brooklyn. Also a golden age of newly constructed greenspace like the Hudson River and East River waterfronts, revitalization of the McCarren Park pool, and Central Park through the CP Conservancy. I think people appreciate it, but may not yet realize that fifty or one hundred years from now people may say that was an incredible period of civic construction.

Website: keithyorkcity.com

Instagram: @keithyorkcity

WORDS Lawrence Ferber

FEATURED IMAGE Eagle on Grand Central Station & Chrysler Building 42nd St Manhattan, New York City

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