If you’ve ever found yourself in the middle of Manhattan, chances are you’ve walked through Herald Square without even realizing it was a "square." Most people just call it "that place with the big Macy’s." Honestly, it’s understandable. The flagship store is a literal behemoth, spanning an entire city block and claiming the title of the largest department store in the United States. But there is a weird, chaotic, and actually kind of charming soul to this intersection that most tourists—and even jaded locals—completely overlook while they’re rushing to catch a train at Penn Station.
The Herald Square Nobody Talks About
First off, let’s clear up the name. It isn't named after a person. It’s named after a newspaper that doesn't even exist anymore: The New York Herald. Back in the 1890s, the paper’s publisher, James Gordon Bennett Jr., moved his headquarters up here to get away from "Newspaper Row" downtown. He was a bit of an eccentric. He had this massive building designed to look like a Renaissance palace, topped with 26 bronze owls with glowing green eyes.
Why owls? Bennett was obsessed with them.
The building is long gone—demolished in 1921—but if you look closely at the monument in the northern part of the square today, you’ll see the remnants. There’s a giant mechanical clock with two blacksmiths, nicknamed "Stuff and Guff," who hammer out the hours. And yes, the owls are still there, perched on the monument, watching the shoppers with those same creepy, stoic expressions.
Why the "Bow Tie" Layout is a Hot Mess
Herald Square isn't a square at all. It’s a "bow tie" formed by the intersection of Broadway, Sixth Avenue, and 34th Street. It’s actually two separate triangles. The northern one is Herald Square, and the southern one is Greeley Square.
Greeley Square is named after Horace Greeley, who ran the New York Tribune. He and Bennett were bitter rivals. It’s a classic NYC move to name two tiny parks right next to each other after two guys who probably hated each other's guts. Today, these spots are basically outdoor breakrooms. You’ll see office workers eating overpriced salads next to tourists who look like they’ve just survived a marathon.
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The Macy’s Factor: What’s New in 2026?
You can’t talk about New York City Herald Square without the red star. Macy’s is the anchor of the neighborhood, and it has been since 1902. But if you haven't been inside lately, it’s changed. Forget the dusty, cramped department store vibes of the early 2000s.
As of early 2026, the store has finally finished a massive, multi-year "luxe" renovation. They’ve essentially turned the first floor into a high-tech beauty playground. We’re talking over 53,000 square feet of cosmetics and perfumes. It’s bright. It’s loud. It’s got virtual try-on mirrors and "niche fragrance" zones that feel more like a spaceship than a retail shop.
Survival Tips for the Flagship
- The Wooden Escalators: These are the real stars. Located on the upper floors, they are original to the building. They creak. They groan. They are terrifying and beautiful at the same time. Do not leave without riding one.
- The Food Situation: Don’t just settle for a pretzel outside. Stella 34 Trattoria on the sixth floor has floor-to-ceiling windows with a killer view of the Empire State Building. It’s one of the best "hidden" lunch spots in Midtown.
- The Crowds: If you go on a Saturday afternoon, you’re asking for a headache. Try a Tuesday morning right when they open. You'll actually be able to breathe.
Navigating the 34th Street Chaos
The area surrounding New York City Herald Square is a transit nexus that handles hundreds of thousands of people a day. Underneath your feet is the 34th Street–Herald Square station. It’s one of the busiest in the system, serving the B, D, F, M, N, Q, R, and W trains.
It is a labyrinth.
If you’re trying to find the elevators—which are a godsend if you have luggage—look for the entrance near the H&M between 33rd and 34th Streets. The station is fully ADA-compliant now, but that doesn't mean it’s easy to navigate. The transfer between the Sixth Avenue lines and the Broadway lines feels like a three-mile hike.
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The Pedestrian Revolution
One thing Google Maps won't always tell you is how much of the "street" isn't for cars anymore. Since the city started the "Broadway Boulevard" project, large chunks of Broadway near the square have been turned into pedestrian plazas.
It’s actually nice.
There are movable chairs, tables, and umbrellas everywhere. In the summer, there are often free dance lessons or chess tournaments. It has turned what used to be a terrifying "death-by-yellow-cab" zone into a place where you can actually sit down and people-watch. And the people-watching here is elite. You’ll see Broadway performers, Elmos taking a smoke break, and high-fashion models all in the span of five minutes.
What Most People Get Wrong
People think Herald Square is just for shopping. That’s a mistake. While you’ve got the flagship H&M, Target, and the revamped Herald Center nearby, the area is also the gateway to "K-Town" (Koreatown).
Just one block east on 32nd Street, you’ll find some of the best food in the city.
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Most people spend three hours in Macy’s and then leave the area, missing out on incredible 24-hour Korean BBQ or hidden karaoke bars. If you’re at Herald Square, walk the extra three minutes to 32nd Street. Grab some bubble tea or a spicy pork bone soup. It’s the perfect antidote to the corporate feel of the big-box stores.
Planning Your Visit: Actionable Advice
If you're heading to New York City Herald Square soon, don't just wing it. It's too big and too crowded for that.
First, check the event calendar for the 34th Street Partnership. They run the parks and often host pop-up markets or free fitness classes in Greeley Square. If it’s holiday season, the Macy’s windows are a given, but also look for the Christmas carousel that usually pops up near 33rd Street.
Second, use the "Secret" Entrance. The main Broadway entrance to Macy's is always a zoo. Use the entrances on 7th Avenue or 35th Street. They are much quieter and get you into the store without the elbowing.
Finally, remember that you are right next to the Empire State Building. Instead of waiting in the massive line there, spend your morning in Herald Square, have a late lunch at Stella 34, and then walk over to the Empire State Building right before sunset.
This neighborhood is a weird mix of old-school NYC history and modern retail madness. It’s loud, it’s expensive, and it’s unapologetically Manhattan. Lean into the chaos, find the bronze owls, and don't forget to look up.