September 05, 2025

Unpacked, Five Questions: The Secret Life of New York's Oldest Businesses

26 minutes

Welcome to Unpacked, Five Questions, a podcast that takes you behind the scenes of one great travel story. In this episode, host Katherine LaGrave sits down with feature writer Harrison Hill, who is working on his forthcoming book The Oracle's Daughter.

For his latest Afar feature celebrating New York City's 400th birthday, Harrison embarked on a borough-hopping journey to visit the oldest family-owned businesses across all five boroughs—from record stores and restaurants to bars and delis beloved by locals.

Harrison reveals how these century-old institutions survive by constantly evolving while maintaining their authentic character, and shares his surprising discoveries about the precarity and resilience of New York's most iconic establishments. He also opens up about approaching his home city of 19 years as a travel destination for the first time.

On this episode you'll learn

Why New York's oldest businesses are both unchanging foundations and constantly evolving enterprises

How iconic places like Katz's Deli and Sylvia's restaurant nearly didn't survive the pandemic

The secret subway trick to see NYC's original City Hall station

What "New Yorkness" really means according to longtime residents and business owners

Why Staten Island should be your next NYC adventure

Don't miss these moments

[02:33] Harrison's revelation about Katz's Deli serving a century-old vegan dish that's back on the menu

[03:33] The easy (but little-known) way to get from Brooklyn to Staten Island via the Verrazzano Bridge

[07:52] The semi-secret subway loop that reveals NYC's original City Hall station

[10:13] Meeting 91-year-old Mike Amedeo, the beloved "mayor" of Casa Amedeo in the Bronx

[14:04] How owning their building saved Sylvia's restaurant during COVID—and the precarity of even iconic NYC institutions

[16:14] Harrison's best advice for New York visitors: "Always look both ways before crossing a one-way street"

Resources

Read Harrison's complete ⁠Afar story about New York's oldest family businesses⁠

Read the transcript of the episode

Follow ⁠Harrison Hill⁠ for more travel and culture writing

Learn more about ⁠NYC's 400th birthday celebrations⁠

⁠Be sure to subscribe to the show and to sign up for our podcast newsletter, ⁠⁠⁠⁠⁠⁠⁠⁠Behind the Mic⁠⁠⁠, where we share upcoming news and behind-the-scenes details of each episode. And explore our other podcasts, View From Afar, about the people and companies shaping the future of travel, and ⁠Travel Tales⁠⁠⁠, which celebrates first-person narratives about the way travel changes us.Unpacked by Afar is part of ⁠⁠⁠Airwave Media⁠⁠⁠'s podcast network. Please contact ⁠⁠⁠[email protected]⁠⁠⁠ if you would like to advertise on our podcast.

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