Holdouts: A NYC Architecture Walking Tour - New York City

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Tour Information

Key Details

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  • Instant Confirmation
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  • Duration: 2 Hrs 30 Mins
  • Language:
  • Departure Time :
  • Departure Details :
    Manhattan, Midtown East
  • Return Details :
    Tour ends around 54th Street and Madison Avenue
  • Cancellation Policy :
    Cancel up to 2 days in advance for a full refund


This 2.5 hour walking tour around the Midtown Manhattan shows-and-tells the fascinating stories of holdoutsthe intriguing side effect of Manhattan's pressure cooker real estate industry: when a property owner (or lease holder) refused to sell to a developer, forced them to rework their plans, and forever changed the city streetscape. Stories, like the elderly lady who never knew any other home; or the poker player-like landlord who overplayed his hand; or the restauranteur whose long term lease (justifiably) demanded budget-busting sums, all add a human dimension to these transactional anomalies. And personal stories that were otherwise lost, are awesomely amplified by the everlasting impression left behind: seemingly ill-planned entrances for skyscrapers, odd shaped buildings, 20-story tall notches in office towers, are just some of the 16 examples of holdouts we'll see.This tour is based on the book, Holdouts! By Alpern and Durst.


  • Step back in time on a history tour
  • Informative, friendly and professional guide
  • Explore the local streets on a walking tour of the city

Know More about this tour

The tour meets inside the lower atrium of 875 Third Avenue. This building itself is a remarkable result of holdouts; its story stands out for the questionable tactics used to encourage the earlier tenants relocate. The first half of the tour heads south on Third Avenue toward Grand Central Terminal, passing 7 holdouts along the way.

At 805 Third Avenue well learn how Smith & Wollensky, the notable steakhouse, was the result of holdouts. At 201 East 42nd Street we'll encounter a corner lot (always a coveted piece of real estate) where a trifecta of greedthe landowner, leasee, and sub-leaseeeach individually held out for such ridiculous sums that the developer walked away and built around them, explaining another odd curiosity in the citys Midtown streetwall. We'll see how a coffee shop with a long term lease resulted in 13-story notch in a midtown office building and one shabby, forlorn looking tenement wedged in among the skyscrapers is the result.

At 42nd Street we head across town passing through Grand Central Terminal, the world famous structure (not encumbered by any holdouts). The second half of our tour goes back uptown, but now on the other side of the tracks of Grand Central.

At 342 Madison Avenue well learn the absurd history of the Canadian Pacific Building, the result of two holdouts along a street: non-adjacent, and neither a corner lot, the effect was a building in the shape of a capital E. It would have financially devastating results. We pass more holdouts as we head west to Sixth Avenue. At 1166 Sixth Avenue we come to one of the most surprising manifestations of a holdout in the citys built environment: the inordinately tall trees of a midblock corporate plaza. Their roots are able to grow deep in the undisturbed earth that was the foundation of a now gone brownstone home. At Rockefeller Center well see one of the most well-known holdouts, the Magnolia Bakery building, a block from Radio City Music Hall. It was once Hurleys Saloon, theirs and a few other fascinating stories are associated with the holdouts of Rockefeller Centers development.

We end the tour at 54th Street and Madison Avenue. It is typical insofar as being a restaurant-type hold out, and yet it is awesome in its effect on the skyscraper at the street level, with the mini-monumental Egyptian-style-battered-walls entrance for the restaurant there today, Papillon.

And each one, each holdouts history has attached to it some human story, an ache, need, or desire that overcame the power of developers pocketbook. Here is a tour that truly humanizes the streets of the city.


  • Professional guide
  • Small-group tour
  • Walking tour


  • Gratuities (optional)

Additional Info

Confirmation will be received at time of booking

A moderate amount of walking is involved

It is recommended to wear comfortable shoes

Subject to favorable weather conditions. If canceled due to poor weather, you will be given the option of an alternative date or full refund

Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough passengers to meet requirements. In the event of this occurring, you will be offered an alternative or full refund