Christmas in Old New York Tour – Walking Tour and Webinar

Get into the holiday spirit with a merry in-person or virtual stroll through The Big Apple!

Tickets: $50 (2-hour and 1.5-mile walking tour through Midtown Manhattan)

Book the Christmas Walking Tour in New York City now!

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“Christmas in Old New York”
Virtual Event – Live Webinar

VIRTUAL WEBINAR – Join us from anywhere you live for this annual festive tradition! Can’t make it for the live virtual event? A recording will be available for 5 days after the tour!

Check back for 2026 Date (New York time)
A recording will be available for five days after the tour.

Book the Christmas VIRTUAL Tour now

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On this merry tour, we’ll take a look at many of New York’s iconic holiday sites, explore its seasonal traditions, and learn how the city created fundamental aspects of modern American Christmas. Our walking tour gets you up close to the bright lights and window displays along Fifth Avenue. While our virtual tour lets you enjoy the festive atmosphere of New York City right from your computer!

Some of the holiday sites and highlights include:

Highlights

• Macy’s Herald Square: the inspiration of Miracle on 34th Street and the birthplace of many holiday shopping traditions.
• Hear how NYC’s writers, artists, and immigrants created countless American holiday traditions, including Christmas trees, classic Christmas songs, and the ubiquitous jolly Santa Claus. 
• Bryant Park: Learn about the park’s annual Winter Village and marvel at the glittering scene (and hear about the park’s sordid past).
• We’ll see the center of the city’s holiday celebration — Rockefeller Center and Radio City Music Hall & the Rockettes.
• We’ll explore the roots of traditions like Sak’s Fifth Avenue’s animated windows, the dazzling Channel Gardens decorations, the towering Rock Center Christmas Tree, FAO Schwarz Toy Store.

Join us on this tour as we explore New York’s historic Christmas tales, traditions, and contemporary holiday spectacles, demonstrating why NYC is America’s quintessential holiday destination.

Led by Bowery Boys Walk guide Jeff Dobbins.

Book the virtual Christmas Tour now – December 10th!

Book the Christmas Walking Tour now!

A recent review on TripAdvisor:

As a big fan of the Bowery Boys Podcast, when I heard they were doing Christmas tours I immediately signed up. The tour was amazing – Craig and Jeff were very knowledgeable and passionate about NYC history and were charming and personable to boot. They even went out of their way to set up a time that worked better for my parents vising from out of town!

Can not recommend this tour highly enough – great way to see the highlights of Christmas in New York.

Duration

Walking Tour: 2 hours
The tour starts in Herald Square and ends at 6th Avenue & 50th St.

Virtual Tour: 90 minutes with Q&A (we will send a Zoom link after you sign up)

(Best suited for adults and most children over 8 years old.)

Please contact us to set up a private tour!