We bring you a classic episode of The Gilded Gentleman, hosted by social and culinary historian Carl Raymond, just in time for a new season of HBO’s The Gilded Age.
In The Real Mrs. Astor, Carl looks at one of the most legendary figures of the period – Caroline Astor, or the Mrs Astor, the ruler and creator of New York’s Gilded Age high society in the early 1870s.
In collaboration with Southern social climber Ward McAllister, Astor essentially created the rules for who was ‘acceptable’ in New York social circles.
But she’s also known for her battles with family members — most notably with her nephew (and next door neighbor) William Waldorf Astor. What was behind her unusual motivations? And in what unusual way did she decide to cap her legacy at the end of her life?
Carl is joined by Tom Miller, creator of the website Daytonian in Manhattan, documenting the history of New York City, one building at a time.
So we don’t know if you’ve heard, but New York City is an expensive place to live these days. So we thought it might be time to revisit the tale of the city’s most famous district of luxury — Fifth Avenue.
For about a hundred years, this avenue was mostly residential— but residences of the most extravagant kind.
Fifth Avenue at Fifty-first Street in the year 1900. Image courtesy Library of Congress
At the heart of New York’s Gilded Age — the late 19th-century era of unprecedented American wealth and excess — were families with the names Astor, Waldorf, Schermerhorn, and Vanderbilt, alongside power players like A.T. Stewart, Jay Gouldand William “Boss” Tweed.
They would all make their homes — and in the case of the Vanderbilts, their great many homes — on Manhattan’s Fifth Avenue.
The image of Fifth Avenue as a luxury retail destination today grew from the street’s aristocratic reputation in the 1800s. The rich were inextricably drawn to the avenue as early as the 1830s when rich merchants, anxious to be near the exquisite row houses of Washington Square Park, began turning it into an artery of expensive abodes.
The Vanderbilt Mansion at 660 Fifth Avenue in 1885, Library of Congress
In this podcast, Tom and Greg present a world that’s somewhat hard to imagine — free-standing mansions in an exclusive corridor running right through the center of Manhattan.
Why was Fifth Avenue fated to become the domain of the so-called “Upper Ten”? And what changed about the city in the 20th century to ensure the eventual destruction of most of them?
The following is a re-edited, remastered version of two past Bowery Boys shows — the Rise and Fall of the Fifth Avenue Mansion. Combined, this tells the whole story of Fifth Avenue, from the initial development of streets in the 1820s to its Midtown transformation into a mecca of high-end shopping in the 1930s.
LISTEN NOW: THE GILDED AGE MANSIONS OF FIFTH AVENUE
People who live in Inwood know how truly special it is. Manhattan’s northernmost neighborhood (aside from Marble Hill) feels like it’s outside of the city — and in some places, even outside of time and space.
Unlike the lower Manhattan’s flat avenues and organized streets, Inwood varies wildly in elevation and its streets wind up hills and down into valleys.
It’s a twenty minute walk from the mysterious “Indian caves” to some of the best Dominican food in New York City. You can experience the ghosts of Gilded Age mansions close to New York’s last remaining forest. Revolutionary War artifacts sit a few blocks away from vestiges of a 20th century Irish community.
Below: Dyckman Street, date approximately 1930s? Note the mansion in the bottom left
In this special on-location episode, Greg Young and producer Kieran Gannon wind their way through the streets of Inwood and through (that’s right) thousands of years of history — from salt marshes to old amusement parks, from ancient arches to Broadway musicals, with ducks and egrets and dogs and beavers making guest appearances along the way.
And since we’re on the subject — what IS the deal with Marble Hill? What do you mean, it’s a Manhattan neighborhood?
This episode was produced and edited by Kieran Gannon.
Below: The Henry Hudson Bridge and “the Big C”
LISTEN NOW: THE STORY OF INWOOD AND MARBLE HILL
Visit the Dyckman Farmhouse! Visit their website for information and a list of events.
Dyckman Farmhouse and an unidentified mansion in the background. Wenzel, Edward, 1892
Cole Thompson and Don Rice leads monthly Lost Inwood talks at Inwood Farm, right off of Inwood Hill Park. In addition Thompson also operates the long running, deeply resource on Inwood history My Inwood. Their book on Inwood history is available in bookstores.
Led Black runs the Instagram account Uptown Collective and now records the new podcast Uptown Voices with Octavio Blanco.
The Bowery Boys Podcast is proud to be sponsored by FOUNDED BY NYC, celebrating New York City’s 400th anniversary in 2025 and the 250th anniversary of the United States in 2026. Read about all the exciting events and world class institutions commemorating the five boroughs legacy of groundbreaking achievements, and find ways to celebrate the city that’s always making history. foundedbynyc.com
Chursh of the Good Shepherd, near Isham ParkThe Isham Park mile marker. Photo Beyond My Ken/Wikimedia The Seaman Drake Arch, seen here in 1920s. Courtesy My Inwood where you can read an article on this remarkable artifact.The arch today, as seen from the train.Inwood historians Cole Thompson and BillyQueen Mallory on her roost atop the Hessian Hut.
FURTHER LISTENING
For more information on subjects discussed on this show, check out these past Bowery Boys podcasts
While you may know the Brooklyn Museum for its wildly popular cutting-edge exhibitions, the borough’s premier art institution can actually trace its origins back to a more rustic era — and to the birth of the city of Brooklyn itself.
On July 4, 1825, the growing village laid a cornerstone for its new Brooklyn Apprentices Library, an educational institution to support its young “clerks, journeymen and apprentices.” This was a momentous occasion in the history of Brooklyn, a ceremony overseen by the Marquis de Lafayette and observed by a young boy named Walt Whitman.
The library was part of a movement — started a century before by Benjamin Franklin— to make knowledge readily available within the young country.
The Brooklyn Museum’s celebratory new exhibition Breaking the Mold: Brooklyn Museum at 200 looks back at its storied origins and eventual growth, encompassing most of the young city’s cultural institutions and soon expanding into a monumental new home next to the new Prospect Park, designed by McKim, Mead and White.
Abigail Dansiger, the Director of Libraries and Archives, and Meghan Bill, the Coordinator of Provenance, join Greg on this week’s show to explain the unusual origins of the Brooklyn Museum and the unique philosophies which inform its exhibitions.
PLUS: A couple genuine mysteries lurk within the new exhibition, including a bottle-shaped niche within the cornerstone and an Egyptologist’s unencrypted notebook.
LISTEN NOW: THE BROOKLYN MUSEUM AND THE BIRTH OF A NEW CITY
Calling all history geeks, New Yorkers and lovers of great storytelling! Greg is bringing you another edition of BOWERY BOYS HISTORY LIVE for July 2nd, 2025.
And this time we’re headed to the fabulous City Winery in the Meat Packing District at Pier 57.
Bowery Boys History Live is a storytelling cabaret of all-true tales and spellbinding secrets from the past, brought to you by a rotating roster of the city’s greatest historians.
And for this show, Greg’s inviving a premier lineup of special guests, including author Elizabeth L. Block (Beyond Vanity: The History and Power of Hairdressing), author and tour guide Keith Taillon aka @keithyorkcity (Walking New York: Manhattan History on Foot), and host of the Gilded Gentleman podcast Carl Raymond.
BOWERY BOYS HISTORY LIVE Gilded Age Golden Girls Edition July 2, 2025, 7:30pm, doors open at 6pm City Winery 25 11th Avenue (Pier 57)
The show’s extra special theme — Gilded Age Golden Girls! Thank you for being a frenemy. A night of storytelling with the late 19th century’s most fascinating characters at its center.
So join us at City Winery on July 2nd, 2025, 7:30 pm, doors open at 6pm
Here’s some images from our last Bowery Boys History Live event back in March at City Vineyard in Tribeca, featuring Greg Young and his brilliant guests Ann McDermott, Krikor Daglian and Kyle Supley
Here’s a little trailer promoting the event with some late 80s sitcom vibes:
In 1939, Robert Moses sprung his latest project upon the world — the Brooklyn-Battery Bridge, connecting the tip of Manhattan to the Brooklyn waterfront, slicing through New York Harbor just to the north of Governor’s Island.
To build it, Moses dictated that the historic Battery Park would need to be redesigned. And its star attraction the New York Aquarium would have to be demolished.
The aquarium was housed in the former military fort Castle Clinton which had seen so much of New York City’s history pass through its walls under the name Castle Garden — first as an early 19th century entertainment venue and later as the Emigrant Landing Depot, which processed millions of newly arriving immigrants.
This valuable link to American history would surely have been lost if not for activists like Albert S. Bard, a revolutionary landmarking advocate who countered and disrupted Moses every step of the way.
Castle Clinton has been a model for creative re-use, serving as a military fort, a concert venue, an immigrant processing station, a city aquarium and a Statue of Liberty/Ellis Island ticket office, now under the operation of the National Park Service.
In this episode, Greg interviews another landmarking superstar — author and civic activist Anthony C. Wood — on the occasion of his new biography of Bard titled Servant of Beauty: Landmarks, Secret Love, and the Unimagined Life of an Unsung New York Hero.
In his research, Wood discovered a personality far more interesting than his public persona and a man with far more at stake than just his beliefs in preservation.
LISTEN NOW: THE BATTLE FOR CASTLE CLINTON
This week’s featured book — Servant of Beauty: Landmarks, Secret Love and the Unimagined Life of an Unsung New York Hero by Anthony C Wood.
Robert Moses, gazing upon his dream bridge project which would have heavily altered Battery Park and completely demolished Castle Clinton.Courtesy New York Public LibraryCastle Clinton in a partial state of demolition after Moses successfully banished the aquarium. Within Castle Clinton are a series of dioramas, dramatically charting the rich history of the building.
FURTHER LISTENING
One of our oldest episodes is on the history of Battery Park and Castle Clinton. Most of the information is contained in today’s new show, but here’s the show if you’d like to listen.
When Prospect Park was first opened to the public in the late 1860s, the City of Brooklyn was proud to claim a landmark as beautiful and as peaceful as New York’s Central Park. But the superstar landscape designers — Frederick Law Olmsted and Calvert Vaux — weren’t finished.
This park came with two grand pleasure drives, wide boulevards that emanated from the north and south ends of the park. Eastern Parkway, the first parkway in the United States, is the home of the Brooklyn Museum and the Brooklyn Botanic Garden, its leafy pedestrian malls running through the neighborhood of Crown Heights.
But it’s Ocean Parkway that is the most unusual today, an almost six-mile stretch which takes drivers, bikers, runners and (at one point) horse riders all the way to Coney Island, at a time when people were just beginning to appreciate the beach’s calming and restorative values.
The lands along Eastern Parkway were unevenly developed in the first few decades. This image was taken between 1903-1910 (Courtesy Brooklyn Museum)
Due to its wide, straight surface, Ocean Parkway even became an active speedway for fast horses. When bicycles became all the rage in the late 1880s, they also took to the parkway and avid cyclists eventually got their first bike lane in 1894 — the first in the United States.
By the 20th century, parks commissioner and ‘power broker’ Robert Moses reinvented the idea of the parkway, in many ways the very opposite of Olmsted’s original intentions. Today the parkways fit awkwardly into New York’s sprawling highway system, making the streets dangerous for neighborhood residents.
Ocean Parkway, late 1890s
And right at a time when Ocean Parkway, in particular, has suddenly become one of the most religious streets in the country.
FEATURING: A tale of two cemeteries — one that was demolished to make way for one parkway, and another which apparently (given its ‘no vacancy’ status) thrives next to another.
LISTEN NOW: PARKWAYS AND THE TRANSFORMATION OF BROOKLYN
Are you free on Saturday, May 31st, 2025? Join Tom and Greg from the Bowery Boys, along with the Gilded Gentleman Carl Raymond, for a three-hour dinner cruise around lower Manhattan through New York Harbor and up to the Statue of Liberty.
CLARIFICATION: As sent in by listener Lewis, today the Garden State Parkway is partially open to some commercial traffic. This does support my claim that the word ‘parkway’ is what you want it to be!
“Garden State Parkway had that restriction for something like the first 50 years. Sometime in the last 15 years, they did start to allow some limited trucks. No semis. Nothing big.”
FURTHER LISTENING
Other Bowery Boys podcasts with similar or related themes:
FURTHER READING
Genius of Place: The Life of Frederick Law Olmsted / Justin Martin Gotham / Mike Wallace and Edwin Burrows Pleasure Drives and Promenades: A History of Frederick Law Olmsted’s Brooklyn Parkways / Elizabeth MacDonald Prospect Park / Ronald P Verdicchio and the Prospect Park Community Study Group Propsect Park: Olmsted and Vaux’s Brooklyn Masterpiece / David P Colley Robert Moses and the Modern City: The Transformation of New York / Hilary Ballon and Kenneth T Jackson
On October 29, 1975, President Gerald Ford walked into a press conference at the National Press Club and, using more precise, more eloquent words than legend remembers, but in no uncertain terms, told New York City to drop dead.
The following day the New York Daily News — the city’s first tabloid newspaper summarized his blunt, castigating speech into one succinct and memorable headline — FORD TO CITY: DROP DEAD.
Of course, the president never actually said DROP DEAD. But his words did signal the severity of New York City’s problem — the city was on the brink of bankruptcy.
In this episode, Greg dives into life in New York City during the year 1975 and the circumstances surrounding its most dire financial crisis, one which threatened the livelihoods of its millions of residents and damaged New York City’s reputation for decades.
Directors Peter Yost and Michael Rohatyn join Greg to discuss their new film on the New York financial crisis Drop Dead City, which uses gritty archival footage and a series of special guests (such as Harrison J. Goldin, Charlie Rangel, Betsy Gotbaum and former Bowery Boys guest Kevin Baker) to explain this complicated story.
If Michael’s name looks familiar, that’s because his father Felix Rohatyn played a critical role in bailing out the bankrupt city.
The film Drop Dead City is currently playing at the IFC Center in New York and coming soon to other theaters and to streaming. Visit their website for additional screening dates.
FURTHER READING
Fear City: New York’s Fiscal Crisis and the Rise of Austerity Politics by Kim Phillips-Fein
One of my all-time favorite books about New York City. A masterful way of summarizing the strange and difficult days of the financial crisis.
FURTHER LISTENING
If you liked the subject of this week’s show, you might like checking out these shows with similar themes
The first part on our Amsterdam/New Amsterdam series — called Empire of the Seas — was just awarded the 2025 Webby Award for Best History Podcast (Individual Episode)
A big thank you to our brilliant producer and editor Kieran Gannon, who pulled this together from about a dozen hours of audio footage. And our fabulous guest Jaap Jacobs, who led us around Amsterdam and allowed us to peer back in time to the 17th century.
Join Tom for an interview with Instagram historian Keith Taillon (@keithyorkcity), whose detailed posts about New York’s history have earned him nearly 60,000 followers and launched a successful tour business.
Keith shares the story behind his remarkable pandemic project of walking every single block of Manhattan in 2020, capturing the empty city in photographs that now appear in his first book, “Walking New York: Manhattan History on Foot.”
From his childhood fascination with urban history to his graduate studies at Hunter College, Keith reveals how his personal journey led him to become one of the city’s most engaging historical storytellers. You’ll hear how he crafts walking tours that go beyond landmark-hopping to explain why New York looks and functions the way it does.
It’s a Bowery Boys Podcast/Marvel Comics Podcast crossover for the ages! Greg was a guest on this week’s episode of the Official Marvel Comics Podcast, talking about the New York City origins of Daredevil.
The character first appeared in Marvel Comics in April 1964 and has always been rooted in the Manhattan neighborhood of Hell’s Kitchen.
Even though the Midtown west side neighborhood is quite different from what it was in the 1960s, the Marvel TV show Daredevil: Born Again series does keep a bit of its original grit intact.
Extra bonus: The series features a contentious mayoral election with controversial political figures and a subplot featuring the rezoning of Red Hook, Brooklyn (which is also being considered in real life).
We invite you to come with us inside one of America’s most interesting art museums – an institution that is BOTH an art gallery and a historic home.
This is the Frick Collection, located at 1 East 70th Street, within the former Fifth Avenue mansion of Gilded Age mogul Henry Clay Frick. The museum containing many pieces that the steel titan himself purchased, as well as many other incredible works of art from master painters such as Rembrandt, Vermeer, Goya, Turner and Whistler.
Frick himself had a rather complicated legacy. As a master financier and chairman of Andrew Carnegie‘s massive steel enterprise, Frick helped create the materials for America’s railroads and bridges.
But his intolerance of labor unions led to a bloody confrontation in the summer of 1892, making him, for a time, one of the most hated men in America.
New Yorkers’ love for the Frick Collection, however, remains far less complicated. The institution, which has been a museum since 1935, allows visitors to experience the work of the great master painters in an often regal and intimate setting, allowing people to imagine the fanciful life of the Gilded Age.
The Frick Collection reopens this month after an extensive renovation (temporarily relocating the collection to the Breuer Building for a few years) and we’ve got a sneak preview, featuring Frick curator and art historian Aimee Ng.
LISTEN NOW: THE STORY OF THE FRICK COLLECTION
The story continues next week on the Gilded Gentleman podcast — Inside The Frick Collection: The Upstairs Downstairs World of a Gilded Age Mansion
Carl talks with managing educator Caitlin Henningsesn about her work researching the domestic staff that worked in the mansion, just who they were and what they did. Caitlin and Carl also discuss, thanks to extraordinary archival records, how the Fricks entertained in a grand Gilded Age style in the very dining room visitors see today.
Photo by Greg YoungPhoto by Greg YoungPhoto by Greg YoungPhoto by Greg YoungPhoto by Greg YoungPhoto by Greg Young
O'Halloran, Thomas J, photographer. New York Post Office. , 1957. Library of Congress
The history of the United States Postal Service as it plays out in the streets of New York City — from the first post road to the first postage stamps.
From the most beautiful post office in the country to the forgotten Gilded Age landmark that was once considered the ugliest post office.
The postal service has always served as the country’s circulatory system, linking the densest urban areas to the most rural outposts, a necessary link in moments when the country feels very far apart in other ways. The early American colonies knew this. Benjamin Franklin knew this The Founding Fathers who placed the postal service within the Constitution knew this.
And inventions such as the stagecoach, the steamship, the railroad, the pneumatic tube and even the electric car have helped keep the mail steadily flowing over the centuries.
The City Hall Post Office at the southern tip of City Hall Park
New York has even played a pivotal role in the development of the American mail service, from the creation of the Boston Post Road (the first mail road which snaked through Manhattan and the Bronx) to the first mail boxes. Even the first postage stamps were sold in New York — within former church-turned-post office in lower Manhattan.
Why are there so many post offices from the 1930s? Why is New York’s largest post office next to Penn Station? And why does New York City have so many individual ZIP codes? And who, pray tell, is Barnabas Bates?
LISTEN NOW: A HISTORY OF THE POST OFFICE IN NEW YORK
A special bonus episode! Two years ago we featured Patrick Bringley on the show, the author of All The Beauty In The World, regarding his experiences as a security guard at the Metropolitan Museum of Art and the life lessons he learned strolling silently past priceless works of art.
How do you transform an off-Broadway stage into the Metropolitan Museum of Art? What life lessons can you absorb from walking around museums?
As it turns out, the routines and responsibilites of a museum security guard can stand in for many types of professions, offering peaceful ritual and possibilies for deeper reflection of the beautiful things surrounding us.
LISTEN NOW: ALL THE BEAUTY IN THE WORLD
Get information and tickets to Patrick Bringley’s new show here and further ticket information here
The Fall of New Amsterdam, painted in 1932 by Jean Leon Gerome Ferris
It’s one of the most foundational questions we could ever ask on this show — how did New York City get its name?
You may know that the English conquered the Dutch settlement of New Netherland (and its port town of New Amsterdam) in 1664, but the details of this history-making day have remained hazy — until now.
Russell Shorto brought the world of New Amsterdam and the early years before New York to life in his classic history The Island At The Center of The World.
His new book Taking Manhattan: The Extraordinary Events That Created New York and Shaped America functions as a sequel of sorts, revisiting the moment when New Amsterdam ceased to be — and New York was born.
Shorto joins Greg and Tom for a very spirited discussion of international warfare, displaced princes, frantic letter writing and ominous warships in the harbor.
At the end of this story, you will not only know how New York — the city, the state, the whole place, from Buffalo to Long Island — got its name, you will know the exact forgotten historical figure who gave it that name.
More details
NIEUW AMSTERDAM OFTE NUE NIEUW IORX OPT TEYLANT MAN by Johannes Vingboons (1664), Stadt Huys, the first City Hall on Pearl StreetThe Duke of York Charter, 1886 illustrationKing Charles II, portrait by John Michael Wright, The Duke of York and future King James II, portait by John Riley
FURTHER LISTENING
Our mini-series on New Amsterdam, featuring Russell Shorto, recorded in 2024
