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Turtle Bay Walking Tour: Bowery Boys Walks NYC Oddities - New York

Turtle Bay Walking Tour: Bowery Boys Walks NYC Oddities

New Yorkeasy

Difficulty

easy

Duration

2 hours

Fitness Level

Basic fitness required; mostly standing and walking on flat city streets.

Overview

Discover four centuries of Turtle Bay’s strange, bold past in a two-hour walking tour by Bowery Boys Walks. From Revolutionary War secrets to celebrity scandals, this trek redefines downtown history with sharp stories and vivid local color.

New York, New York

Turtle Bay Walking Tour: 400 Years of East Midtown Oddness

2 hours • About 1 mile • Ages 16+

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Adventure Photos

Turtle Bay Walking Tour: 400 Years of East Midtown Oddness photo 1

About This Adventure

Embark on a captivating 2-hour journey through Turtle Bay, East Midtown's quirky history. Discover tales of iconic figures like John Lennon and Marilyn Monroe, explore the neighborhood's bizarre past, and uncover secrets from the Revolutionary War to modern scandals. This unique tour promises unforgettable stories and intriguing insights into New York's hidden gems.

A terra-spin through 400 years of East Midtown oddness

(Best suited for adults and older teenagers that have a strong interest in New York history.)

Duration

2 hours, about 1 mile

Overview

“I am still not clear how I got here. There are no turtles. There is no bay.” – author Kurt Vonnegut on the East Midtown block where he lived for 40 years

Turtle Bay is much more than fancy apartments, tiny dogs and tinier-tipping diplomats. This neighborhood, nestled between Lexington Avenue’s Grand Central Terminal and the East River’s United Nations, is so (quietly) weird that it makes Twin Peaks, WA, look like an equally fictional Mayberry, NC.

Here’s licensed tour guide, TB local, longtime New York Times museums-and-old-bars contributor and overall media monster, Bill Schulz’s, version of a trailer…

This is the address where Nathan Hale regretted he had but one life to give, right before being hung as our first (albeit wholly ineffective) Revolutionary War spy.

John and Jackie Kennedy honeymooned here, Paul Newman and Joanne Woodward’s marriage began here while Joe DiMaggio and Marilyn Monroe’s union ended here. All while Andy Warhol’s first Factory appalled uptight locals.

Within this zip code, Bernie Madoff’s billion-dollar Ponzi scheme was hatched, John Lennon’s “lost weekend” was dispatched, while writers-in-residence: Truman Capote, Stephen Sondheim and E.B. White’s plot points were attached.

Katherine Hepburn, Elizabeth Taylor, Frank Sinatra, Senator Robert F. Kennedy, President Dwight D. Eisenhower, Greta Garbo, General Douglas MacArthur and Johnny Carson called Turtle Bay home, (mostly on, or off, 49th street), Buddy Holly, Richard Harris, along with Elizabeth Taylor, tippled within these storied taverns, (mostly at the 140-year-old PJ Clarke’s), while John Gotti murdered here (mostly at Sparks Steakhouse).

Highlights:

  • Your “Why is East Midtown called Turtle Bay?” queries…(is it an English bastardization of the Dutch word deutal, meaning “bent blade”, per this harbor’s knife-like shape, a main source of cuisine for resident Lenape tribes or an ode to four, Manhattan-based, teenage reptiles, named after Italian Renaissance artists, who fell into nuclear ooze and became ninjas/mutants?)…will all be answered.
  • The story behind why a manic mob destroyed an entire block, between 45th and 46th Streets, sparking the infamous draft riots of 1863.
  • A mid-19th-century-built stable and dairy that currently hosts a club devoted to experimenting with all manner of mind-altering psychedelics.
  • A certain subway grate that hosted a certain upskirt shot of a certain Hollywood icon. Salacious Secret Service stories, (every President, within the last two centuries, has had a hotel stay within Turtle Bay).
  • Ladies of the evening and the UN diplomats that love them, (i.e. why this area is quietly a hooker haven of Manhattan).
  • The home of a legendary, female journalist who was the first to detail Nazi atrocities whilst also calling out Charles Lindbergh as, less a hero, and more a dirty Hitler apologist.
  • The strange saga of New York Jets Hall-of-Famer, Joe Namath’s, attempt to own a sensationally sleazy singles bar following his 1969 Super Bowl win.
  • Insane anecdotes regarding famous tenants within The Waldorf Astoria.

Please Note

This tour takes place in and around East Midtown in the Turtle Bay neighborhood. Exact start location will be sent via email after you sign up.

*Tours take place rain or shine ​— dress for the weather!

Private Group: Please contact us for pricing and availability

Adventure Tips

Wear comfortable walking shoes

The tour covers about a mile on city sidewalks with frequent stops—footwear that supports steady walking is key.

Bring weather-appropriate layers

Tours run rain or shine, so dress accordingly and carry a compact umbrella or sun protection depending on the forecast.

Arrive early for easy meeting

Plan to arrive 10 minutes before the start time at 915 3rd Ave to ensure a prompt departure and smooth check-in.

Ideal for ages 16 and up

This tour’s content delves into mature themes, including political scandals and historical controversies.

Local Insights

Wildlife

  • Urban squirrels darting through tree-lined blocks
  • Pigeons clustered near historic sidewalks and street corners

History

Turtle Bay was once home to Revolutionary War spy Nathan Hale and later became a hub for artistic, political, and criminal figures shaping NYC's 20th-century story.

Conservation

While primarily urban, Turtle Bay benefits from efforts to maintain green spaces and pedestrian-friendly streets, contributing to a sustainable city environment.

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Adventure Hotspots in New York

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Supports steady movement along city sidewalks and during frequent stops.

Weather-appropriate jacket

Essential

Keeps you warm and dry in variable urban weather.

spring|fall|winter specific

Sun protection (hat and sunscreen)

Essential

Protects your skin during sunny, exposed stretches of the walk.

summer specific

Water bottle

Helps you stay hydrated during warmer weather.

summer specific