Mapping the History of New York on Instagram

Historian and writer Keith Taillon walked every block in Manhattan to document the city's past and present. His account, @keithyorkcity, is an incredible treasure trove of discovery, intrigue, and time travel.

Washington Square Tree, circa 1910, is now 350 years old.

@keithyorkcity, 17,500 followers.

As 2019 came to a close, Keith Taillon, 33, was feeling unfulfilled. “It was that down-and-out feeling that can creep up in the week between Christmas and New Year’s Eve. I didn’t feel like I’d done anything remarkable,” the Harlem resident says. To soothe his angst, he decided to walk the length of Manhattan, all 14 miles, with his partner Clinton to end the year on a high note. “I was inspired by an episode of “Broad City” in which Abbi and Ilana walk Broadway for Abbi’s 30th birthday.”  

Upon waking up the next day, Taillon, a historian and writer by trade, decided to keep the ball rolling. He pledged to walk every New York City block in 2020, if for no other reason than he loved being outside. Then Covid hit. “It became my coping mechanism and a way for me to keep my finger on the pulse of the city as it went through such an unprecedented trauma,” he says. “I watched stores close, outdoor dining appear, crowds ebb and flow with the local infection rates. In the end, I feel like the project kept me grounded and sane during a particularly difficult year. As a bonus, I got to explore corners of Manhattan I’d never otherwise visit. I learned so much and got to share that sense of discovery with my Instagram followers.”  

The first Macy’s Thanksgiving Day Parade, 1924.

Taillon’s Instagram account has become essential viewing for anyone interested in New York’s heritage, the effects of gentrification on cities, period architecture, American history, and what the past can tell us about the future.

On any given day his followers might discover an exposé on a tree in Madison Square Park that is older than the Revolutionary War, an account of the great blizzard of 1888, stories about indelible city characters and erstwhile landmarks, or retrospectives on profound cultural moments such as the 1959 arrival of the groundbreaking Frank Lloyd Wright–designed Guggenheim Museum and the first Macy’s Thanksgiving Day Parade almost a century ago.

Each post is a time capsule to a bygone era, complete with historical photos, maps, and newspaper clippings sourced from the New York Public Library and the New York Times, informational overlays, and deep journalistic captions. It’s a remarkable record of New York, retrofitted for digital consumption.

The alluring part of Taillon’s storytelling is his ability to document and mourn the things we’ve lost (the original locations of Penn Station and Metropolitan Museum of Art), provide context for what we still have (Grand Central, Chrysler Building), while offering a roadmap of sorts for where we need to go.

I want people to understand and appreciate the past so they can make informed decisions about the future,” he says. “I think we’re faced with the beginning of a new era in New York’s history. The way people refer to the 1929 stock market crash or the 1977 blackout or even 9/11, people will refer to the 2020 pandemic for decades to come. And we’ll be judged based on what sort of city we build from this. History tells me that as painful as everything is right now, I can be optimistic that better days are ahead.”

Here, we speak to Taillon about the destruction of New York’s architectural heritage, his favorite landmarks still standing, and the benefits of storytelling on Instagram.

The original Penn Station, 1911.

I’m in awe of the depth and dedication of your account. What is your process for each post and how long does each one take? Do you decide on a subject far in advance and how arduous is the research?  

Thank you! That really means a lot, because I do take pride in the quality and accuracy of my work. I wish I could tell you I had a formal process, but I just don’t. I’ve got such an endless backlog of stories floating in my brain that I’d like to tell, that it’s a bit scattershot as to what actually gets pieced together into a post for Instagram. I might be researching one story and stumble on a totally different one that I end up posting first. Or I might wake up thinking about a building I saw once, and spend the rest of the day untangling its history. I like to offer a fresh perspective on these stories, too, so I try not to just regurgitate the same content that’s available in every corner of Google. I take my time, finding unusual photos, quotes, floor plans, and maps, knitting together a perspective that maybe people haven’t been shown before. That takes hours. Truly involved stories can take days. There’s no content calendar, and I rarely know what post I’ll do next. I’m trying to be more organized, but I also like wandering down whatever trail my research leads me.  

Where do you source all of the historical images and newspaper clippings from?

My two most reliable sources are the New York Public Library (for images) and The New York Times (for newspaper clippings). The Library has hundreds of thousands of images digitized, many available for high-resolution download, including thousands of old maps of the five boroughs which are invaluable to me as a researcher. The Times has something called the “Times Machine,” which has every single issue of the paper from 1851 to 2002 available for searching and browsing. It’s the most incredible tool, and it’s included in the price of a normal digital subscription. Aside from those, I’ve found the Library of Congress to be reliably terrific for both images and newspapers, though its online search function leaves something to be desired. I’ll often find what I’m looking for eventually, but it’s not quite as intuitive as the NYPL or the NY Times. 

The New Amsterdam Theatre interior, before 1914.

One thing that you do that I love is pegging current events to the past. When New York’s first snowfall arrived this year, you had a post up about the blizzard of 1888. Does the news often influence your editorial decisions? 

The blizzard of 1888 is such an incredible event in New York City’s history. It paralyzed most of the northeast, and New York in particular took drastic steps over the next twenty years to make sure it was never so vulnerable again. It’s why our power lines are underground, and it’s part of the reason why the subway was built: the old overhead cables and elevated trains were devastated by the blizzard. I’m constantly comparing current events to the past, mining for clues, thinking I might be able to understand our future if I understand how past generations dealt with theirs. We’re eight years past Superstorm Sandy now, and I’m not sure we’ve been quite so decisive as our forebears in making sure we’re protected from a future recurrence. So in that sense, yes, the news influences me. But mostly I want people to understand and appreciate the past so they can make informed decisions about the future.

The blizzard of 1888.

One of my favorite content series on your account is Lost Places. It draws out all the nostalgic feels. It’s also kind of sad when you look at some of the gorgeous structures we’ve destroyed and what has replaced them. I live in Brooklyn and it seems like every day I see a brownstone coming down so a modern condo can take its place. What’s your view on preserving historic architecture versus making room for the new, and how good of a job do you think local government is doing in protecting the city’s historic buildings?

I struggle with this question as I walk around the city. I moved to Manhattan in 2010. The past decade has been, unquestionably, the most aggressive era of development this island has seen in at least two generations. There’s a theory that the concept of historic preservation only arose when people realized that what was being demolished was better than what was replacing it. I can make peace with the loss of old buildings when they’re replaced by something beautiful, human-scaled, and enduring. Unfortunately, I feel that the city has lost far more than it has gained lately. Preservation often comes too late, if at all. I live in Harlem and have watched this neighborhood be stripped of its architectural heritage, one building at a time. If local officials ever turn their attention up here, they’ll find it’s too late to save a staggering number of places that should have been preserved, but have instead been replaced by cheap mediocrity.

The original Met with Richard Morris Hunt's 5th Ave entrance, 1909.

The thing that instantly stands out about your account is your phenomenal storytelling. As a writer and historian by trade, how do you like the format of Instagram? Was it difficult to organize your thoughts at first in terms of the in-feed captions, the bitsy photo overlays, Stories, highlights, AMAs, etc? You seem to have mastered it.  

Learning to tell often long and complicated stories through Instagram has been a long process. Scroll back in my feed and you’ll see how many times I’ve changed my storytelling style, trying to find the best way to get the most information across clearly. I like the ease with which my storytelling can reach such a broad audience on Instagram. It forces me to condense stories down to a finite number of words and images, which can be frustrating. Many people might never read a 200-page dissertation on, say, the architectural history of the Met Museum, but they will scroll through 10 slides explaining it to them in layman’s terms. To me, that’s a win. If I can engage with people in ways they can understand, and in that way help them to appreciate the history that’s all around them, then I feel like I’ve succeeded in doing something good. The social aspect of Instagram is one of the greatest surprises of this whole endeavor, actually. The comments and messages I get from people every day make all the time and effort worth it. Knowing people look at the city differently because of my posts, I couldn’t be happier.

As a historian, your eye is trained on the past. Do you like modern architecture, design, or art at all? If so, who or what are some of your favorite things in those realms? 

This is tough because my brain is so focused on the past most of the time. I’m thrilled by what I see happening in the art world today, particularly among BIPOC and LGBTQ+ artists. Specifically, I have been enthralled by the works of Toyin Ojih Odutola, Salman Toor, and Louis Fratino. As for architecture, the trend has been toward glass boxes and expensive gimmicks for a long time now. I see exciting voices emerging, like the firm Tropical Space in Vietnam and New York-based architect Sharon Davis. Both exemplify a shift toward more human-scaled, human-centered architecture which is sensitive to its local culture and environment. 

Madison Square Garden, designed by McKim Mead & White, 1893.

What is your favorite architectural style? Architects? 

I don’t have a favorite style. What I look for in a building is a sense that it was built with care and endurance. The old Dutch-style Dyckman Farmhouse in Inwood brings me as much joy as the Chrysler Building, an Art Deco masterpiece built two centuries later. The buildings couldn’t be more different, but both were built thoughtfully in styles and materials contextual to their eras, but which have stood the test of time. That said, I also don’t have favorite architects. I’m an admirer of Henry Hobson Richardson and the firm of McKim, Mead & White. Give me elaborate exterior stonework and sumptuous interior woodwork any day and I’m a fan. 

If you had to choose, what are your five favorite buildings in New York? 

That’s really tough, and my answer probably changes yearly or even monthly. My favorite places in New York are those that welcome everyone and make them feel like they’re important, valued, and part of the greater New York community. With that in mind, the main Fifth Avenue Branch of the New York Public Library is probably my favorite, along with Grand Central Terminal. I also really love the Metropolitan Museum of Art. For my last two, I’m going to cheat a bit: I love the city’s Broadway Theaters (all 44 of them!), and I love Central Park (while not technically a building, it was designed by architects and it is surrounded by a wall, so I stand by it). 

Central Park, circa 1904.

If you could bring back any building, which one would it be? 

I have to say the old Penn Station. No other building carries the weight of loss that Penn Station does for the city. New York’s entire biography could be written in two volumes: everything leading up to the demolition of Penn Station and everything that’s happened after. The entire concept of historic preservation was birthed in the wake of Penn’s destruction, and all landmark demolitions since then are compared to it. We’ve spent the better part of the last 50 years trying to think up ways to make up for the loss of Penn, with the new Moynihan Train Hall the latest and most ambitious attempt at bringing some sense of grandeur back. But if I could, I’d bring back the original as it was in 1910: a testament in granite to the city’s hubris and optimism.

What have you learned about New York City that you didn’t know before your quest to walk every street?

I’ve learned what a community Manhattan really is. Each neighborhood really functions as a small town, which is something I knew in theory but hadn’t paid much attention to in practice. Walking the island in 2020, this was even easier to see since there were virtually no tourists. I got to see New York full of New Yorkers going about their daily lives. There isn’t a corner of this island where people aren’t walking their dogs, running to their bodega, buying lottery tickets, grabbing a coffee, moving in and moving out, planting flowers in tree beds, waving to neighbors, or taking their kids to school. For all its uniqueness, Manhattan really is an island full of little villages, full of regular people going about their lives. That’s wonderful to me.

The New York Public Library 5th Avenue branch, 1911.
Grand Central Terminal. 1934.

As someone who is proficient in the different periods of New York’s history, I’m interested to hear your perspective on COVID-19 and the city’s post-pandemic prospects. Things are pretty bleak right now. We’ve lost some iconic restaurants, bars, hotels, and more. However, if there’s one thing I took away from the Ken Burns documentary, it’s that New York always adapts and comes back. What can history tell us about what’s to come after this period and what is your outlook? 

The pandemic has been brutal for the city. In four centuries of existence, New York has endured disease, war, economic collapse, floods, blizzards, depopulation, and all forms of calamity imaginable. It’s always rebuilt and recovered. What matters now is how we move forward from this over the next generation or two. I wish I could say things would go back to “normal,” but I don’t think that’s what we’re looking at. I think we’re faced with the beginning of a new era in New York’s history. The way people refer to the 1929 stock market crash or the 1977 blackout or even 9/11, people will refer to the 2020 pandemic for decades to come. And we’ll be judged based on what sort of city we build from this. History tells me that as painful as everything is right now, I can be optimistic that better days are ahead.

It is obvious that a tremendous amount of work goes into your Instagram account. Do you plan to evolve it into more? I’ve seen some mentions of walking tours…Are you still writing and doing other work? Is the best way to support your work through your account on Patreon? 

Patreon is a terrific way to support me! Every dollar contributed directly supports me and allows me to spend my days researching and writing. I’m also hoping to get a book put together about New York: part photo album, part history lesson, part NYC guidebook. So if any agents or publishers read this and are interested, contact me! Additionally, I recently launched a shop on my website,, where I sell photo prints and postcards and whatnot. I’ll also be offering walking tours soon. Basically, I love doing this sort of work, and am hoping to someday make a living doing it. Any support goes a very long way toward helping me reach that goal.

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