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Harlem / Jazz

Billie Holiday's Harlem & the Birth of the Jazz Age

Walk the streets that made Lady Day — and the era of American music she helped define.

Mark leading the Billie Holiday tour in Harlem
Photo: Klaus-Peter Statz/Untapped New York
Photo: Klaus-Peter Statz/Untapped New York
Duration2 hours
Group SizeUp to 20 guests
CancellationFlexible
NeighborhoodCentral Harlem
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About This Tour

I've lived on Strivers Row for over 25 years. These blocks aren't just a backdrop for this tour — they're my neighborhood. I've walked past the buildings on this itinerary thousands of times, and every one of them has a story I can't stop thinking about.

The Jazz Age in Central Harlem was one of the most concentrated explosions of creative genius in American history. It happened alongside the Harlem Renaissance — the flowering of visual art, poetry, and prose — but the music was its own force entirely. In the 1920s and 30s, a few square blocks of Harlem were the center of the musical universe. This tour takes you there.

We follow Billie Holiday from her first footsteps in New York City to the stages where she found her voice — and we stop along the way at the clubs, the parlors, and the street corners where jazz was invented, argued over, and perfected. You'll hear about Duke Ellington's New York debut, about Ella Fitzgerald's discovery, about the remarkable musicians who lived and gathered on Strivers Row. And you'll see 133rd Street — the original "Swing Street" — where the prohibition-era clubs had names like Pod & Jerry's, the Hot-Cha, and the Uptown Club.

This is the Harlem most visitors never see. Come find it.

What You'll See

  • Follow in Billie Holiday's footsteps — from her first residence in New York City to the site of her earliest performances
  • Hear the stories of legendary jazz clubs, including the spot where Ella Fitzgerald was discovered and made her name
  • Visit the site of Duke Ellington's first New York City gig
  • Stroll through Strivers Row and see buildings where Fletcher Henderson, Eubie Blake, W.C. Handy and other jazz giants lived and gathered in the 1920s
  • Peer into the modest parlor room that gave birth to the first Black-owned record label in America
  • Walk 133rd Street — the original "Swing Street" — and hear the stories of the colorfully-named clubs that made it the top jazz destination in New York during Prohibition