• Flatiron Building - The tour kicks off with a comprehensive overview of the area’s history and the city’s expansion uptown. Photographs illustrate the transformation from farmland to a chic urban center.

The tour delves into the history of the Astors, the establishment of the first Waldorf=Astoria, and their social connections with families like the Vanderbilts, who represented the new industrial wealth.

• Madison Square - Photographs enrich a brief walk and discussion around Madison Square, highlighting the histories of Met Life and the original Madison Square Gardens during the Gilded Age.
• Broadway Theatre - The tour navigates the remnants of the long-lost city, from the era when telephones and electricity were novel and uncommon in homes. It was the age of department stores, apartment buildings, and office towers, introducing new lifestyles for the emerging middle class. Each intersection at Madison Square offered a unique class-based commercial attraction, including a red-light district above 23rd Street and west of Broadway.

The tour explores the upscale carriage trade shops along Broadway, featuring historic buildings like Lord & Taylor and Arnold Constable & Co, among others.

• Fifth Avenue - Below 23rd Street, Fifth Avenue boasts a unique development history unlike any other in the city. Here, the Garment District was “diverted” from Midtown, creating a distinct built environment.
• Sixth Avenue (Avenue of the Americas) - Sixth Avenue was the middle-class shopping hub and still showcases its impressive array of buildings as the city transitioned from cast iron to steel frame construction. Notable buildings include: Seigel-Cooper, B. Altmans, Hugh O’Neill’s, and Adams Dry Goods Store.
• Broadway - Above 23rd Street, history takes a sharp turn as we enter the old Tenderloin, an area once filled with concert-saloons, brothels, and gambling halls, when home entertainment centered around the piano.
• Flatiron District - Returning to Fifth Avenue, the tour explores significant architecture, featuring early experiments in multi-family housing: apartment-hotels, French flats, bachelor flats, and early co-ops. Notable buildings include: the Wilbraham, Holland House, Seville, and the Martha Washington.
• Madison Square Park - The tour concludes in Madison Square Park with intriguing histories, including the Worth Monument, Delmonico’s, and the old Brunswick Club.

• Expert guide

• Gratuities

Visitors will gain an understanding of how compact the Gilded Age city of New York was. Shopping and theater districts for the upper and middle classes were located just a block or so apart. Additionally, innovations such as apartment buildings, department stores, and office towers were at their peak around Madison Square, coinciding with the advent of telephones and electricity.

The most intriguing aspect is the close proximity of these venues, from the upscale shops and residences of families like the Roosevelts, Astors, and Schermerhorns, to the blocks of illicit and often lively nightlife activities in the old Tenderloin, just a few blocks away.

This tour is a remarkable exploration of the Gilded Age city of New York around Madison Square.

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