Midtown Manhattan Holdouts 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.

Meeting Point

875 3rd Ave

875 3rd Ave, New York, NY 10022, USA

Lower level lobby

What's included:

• Professional guide

What to expect:

Duration: between 2 hours and 3 hours

TPR Holdings

875 3rd Ave, New York, NY 10022, USA

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.

15 minutes

Lipstick Building

Lipstick Building, New York, NY 10022, USA

A fascinating ego building

Pass by without stopping

Citicorp Center

601 Lexington Ave, New York City, 10022-4611, New York

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.

Pass by without stopping

Wollensky's Grill

201 E 49th St, New York, NY 10022, USA

An old buggy whip factory, and a holdout.

5 minutes

Amster Yard

211 E 49th St, New York City, 10017-1501, New York

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!

5 minutes

Sparks Steak House

210 E 46th St, New York, NY 10017, USA

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

5 minutes

Chrysler Building

405 Lexington and 42nd St., , New York City, 10174, New York

Stunning views of this stunning landmark are had along here.

Pass by without stopping

United Nations Headquarters

46th St & 1st Ave, New York City, 10017-3507, New York

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

Pass by without stopping

42nd Street

New York City, New York

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

5 minutes

Grand Central Terminal

89 E 42nd Street, , New York City, 10017-5503, New York

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.

5 minutes

One Vanderbilt

1 Vanderbilt Ave, New York, NY 10017, USA

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

Pass by without stopping

Brooks Brothers

, , New York City, 10028, New York

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

5 minutes

Bank of America Tower

Bank of America Tower, 1 Bryant Pk, New York, NY 10036, USA

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

Pass by without stopping

The Roosevelt Hotel

45 E 45th St, New York, NY 10017, USA

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.

Pass by without stopping

Diamond District

Ave of the Americas & W 47th St, New York City, 10036, New York

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.

Pass by without stopping

Rockefeller Center

45 Rockefeller Plaza, New York, NY 10111, USA

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

10 minutes

Papillon Bistro & Bar

22 E 54th St, New York, NY 10022, USA

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.

5 minutes