• Flatiron Building - This walking tour explores the Gilded Age, a period when this neighborhood thrived as a fashionable world-class city center from the 1860s to the 1920s. The tour provides context on the broader history of the city and Madison Square’s role in its development.
• Madison Square Park - At the intersection of Fifth Avenue, Broadway, and 23rd Street, this area was the heart of the Gilded Age. It emerged as a new social, political, and cultural hub as the economy surged during the Industrial Age. The old elite, like the Astors, were outpaced by new industrial wealth, such as the Vanderbilts, with Madison Square at the forefront of this social transformation.

In addition to the social and cultural history of the Gilded Age, the subsequent era and its buildings are also intriguing. These commercial structures have a fascinating history, and their development helps make sense of New York’s architectural landscape.

• Fifth Avenue - The tour continues along Fifth Avenue between 23rd and 18th Streets, examining the buildings to understand their development. The tour explores when these buildings were constructed, for whom, and how they evolved.

Here, New York’s “signature” building type, the late 19th-century “state-of-the-art” steel-frame manufacturing loft building, often in the “elongated” Beaux Arts style, is examined in detail.

Later known as Paternoster Row for its mission office buildings and publishing operations, this street of class and wealth was transformed into office buildings housing publishers, architects, textile manufacturers, and piano showrooms. It was once a thriving business district in a long-forgotten upper-class neighborhood.

• ABC Carpet & Home - Broadway between Madison and Union Square spans just six blocks and is a quiet, hidden gem in New York City today. This area is rich in fragmented French Second Empire, Beaux Arts, and Neo-Classical relics. During the Gilded Age, it was a high-end shopping district known as the “carriage trade” blocks. This part of the Ladies’ Mile Historic Shopping District lacked elevated trains and horse car rails, allowing women to step from carriages to shop along this narrow and quiet stretch of Broadway. It remains a treasured location in the city today.
• Theodore Roosevelt Birthplace National Historic Site - The tour explores how the former President’s life fits into the broader history.
• Sixth Avenue (Avenue of the Americas) - The blocks of Sixth Avenue from 18th to 23rd Streets are a well-preserved collection of beautiful old department stores and shopping emporiums. This area was the middle-class shopping district, yet some establishments were worthy of the carriage trade.

The tour delves into the history of the department stores that once brought vibrant energy to these blocks, while also appreciating the architectural relics and ruins that tell the story of earlier times and previous occupants.

• Sixth Avenue (Avenue of the Americas) - Crossing 23rd Street heading north, the tour enters the old “Tenderloin,” a district of adult entertainment before the era of radio and television. It is surprising today that a district of saloons, brothels, and gambling halls was so close to venues for respectable activities that attracted respectable citizens.

It’s not surprising that fewer buildings survive on this side of 23rd Street, as red-light districts are rarely preserved. The remaining structures, besides venues and houses of ill-repute, housed middle and lower-middle-class neighborhoods, as well as large African American and Jewish communities. These blocks are linked to some of the city’s most intriguing, deviant, and scandalous stories.

• Tin Pan Alley - Tin Pan Alley is one of New York’s latest historic districts. For a brief period, the heart of the American music industry was concentrated in a few buildings along 28th Street between Fifth Avenue and Sixth Avenue.

Here, sheet music flourished, and popular music emerged. The early marketing methods of music promoters, including various forms of plugging, began here.

• Hotel Wolcott - Crossing Broadway, the tour immediately senses the historical shift in the street wall as it moves just a few feet to Fifth Avenue, the upper-class part of town.

The Wolcott Hotel was one of over a dozen fine Gilded Age hotels in the area, many now converted to SROs and city housing.

• Empire State Building - Once the site of the original Waldorf-Astoria and the residences of the Astor brothers, the Empire State Building was the tallest building in the world for 40 years.
• Fifth Avenue - The final leg of the tour covers the blocks between the Empire State Building and the Flatiron Building. These blocks are a Rosetta Stone of New York history, featuring buildings from every era as the city expanded uptown.
• 230 FIFTH ROOFTOP BAR NYC - The tour concludes at a convenient point in Madison Square for the guests.

• Professional guide

• Gratuities

This 2-3 hour guided walking tour around Madison Square Park seeks out what’s left to be found of the Gilded Age city. On this tour we read the architecture and decode the street walls in a neighborhood that was once the New York’s city center at the height of the Gilded Age. Where the city came from (Soho), and where it moved to (Times Square, Museum Mile, and the shops of Fifth Avenue) is integral to understanding how New York, and Madison Square, developed. You’ll learn answers to questions you didn’t know you had about New York City, and leave with the deeply satisfying sense of understanding a city that author James Baldwin called ‘spitefully incoherent’.

For a full refund, cancel at least 24 hours before the scheduled departure time.