Holdouts: A NYC Architecture Walking Tour

This 2.5 hour walking tour around the Midtown Manhattan shows-and-tells the fascinating stories of holdouts—the 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.

1. 1

   Stop 1

   15 min

   We start in lower lobby of this distinctive building where we'll lay the groundwork for the tour, where we'll go and what we'll see. The building itself is the result of holdouts, and our first subject.

2. 2

   Stop 2

   Pass by

   A fascinating ego building

3. 3

   Citicorp Center

   Pass by

   Not a holdout, but a fascinating story is associated with the construction of this building, whose main pillar supports are not in the corners, but in the middle of the side.

4. 4

   Stop 4

   5 min

   An old buggy whip factory, and a holdout.

5. 5

   Amster Yard

   5 min

   If this oases is open at the time of the tour, we stop in for a moment. A time capsule where histories clash and the city meets the suburbs - - a much earlier one!

6. 6

   Stop 6

   5 min

   This notorious site of a mob hit is next door to an interesting holdout.

7. 7

   Chrysler Building

   Pass by

   Stunning views of this stunning landmark are had along here.

8. 8

   United Nations Headquarters

   Pass by

   We view the Secretariet Building down the block as we continue to pass and discuss holdouts and how they've influenced the streetscapes today.

9. 9

   42nd Street

   5 min

   We end our downtown part of the walk at 42nd Street, where a single holdout survived history.

10. 10

    Grand Central Terminal

    5 min

    As we make our way to the west side and the uptown portion of the tour we will pass through Grand Central. While not associated with a any holdouts, a mini-tour of this iconic landmark is very possible.

11. 11

    Stop 11

    Pass by

    This city-in-a-building was still under construction at this writing.

12. 12

    Brooks Brothers

    5 min

    This historic New York City institution had a holdout as a neighbor.

13. 13

    Stop 13

    Pass by

    We view this crystal shard-iceberg mashup of a building from the side

14. 14

    Stop 14

    Pass by

    We pass by this sole survivor of Terminal City, from a time before air travel when Grand Central linked to three hotels to receive cross-country travelers. We continue our tour passing fascinating ways holdouts have changed the look of the city.

15. 15

    Diamond District

    Pass by

    Worth noting the block where $440 million in diamonds are traded daily. The entrance a block to the north as we cross Fifth Avenue is flanked by 12' diamond sculptures.

16. 16

    Stop 16

    10 min

    Rockefeller Center's rich history includes a number of interesting, thought provoking holdouts.

17. 17

    Stop 17

    5 min

    We end the tour here, one of the most compelling examples of a holdout, and is more appropriately a hold-IN. Here a restaurant proprietor negotiated additional square footage to expand his restaurant into the future skyscraper. You can enter the skyscraper today and stand within the walls of a 19th century brownstone.

• Wheelchair accessible
• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Infants are required to sit on an adult’s lap
• Travelers should have at least a moderate level of physical fitness

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