Here’s the northern end of what used to be called Ladies’ Mile, where from the Civil War to about 1910, New Yorkers came to buy hats, coats, accessories, and other items that every New Yorker couldn’t live without.

Over time, Sixth Avenue extended north, was widened, covered with an elevated train, and became a bit of a speed corridor for much of its way north. Even with the train long gone, some of Sixth Avenue is pretty unpleasant and acts more as a barrier between neighborhoods than a coherent link. But it’s still fine.

Now, you can pull a neighborhood name from a hat and not be wrong: Flatiron? NoMad? Silicon Alley? Let’s just go with Chelsea.

Here, the Adams Dry Goods Building dominates the west side of the street, while a motley mishmash of smaller 19th-century buildings line the east side like Gilded Age gumballs. The omnipresent chains (there’s a Cava, Chipotle, McDonald’s, Michaels, Starbucks, etc.) are gnawing away at the character.

But our menu is still strong: from gum to seaweed snacks to late-night pastrami, there’s always been a lot to chew on, as you’ll see.

Street view here.

Hey, it’s Trader Joe’s!

Way before it became a palace of produce, the building’s roots went back to the 1880s when Samuel Adams (not that one) returned from Colorado, where he’d sought gold and found public office, then opened a dry goods store here in 1885.

As he acquired more buildings on this stretch, he eventually replaced them with this Beaux-Arts department store with rich details and arched second-floor windows designed so riders on the elevated train could peek inside at the merchandise.

On a late afternoon in May 1906, a faulty rooftop water tank burst under pressure and fell through the skylight, sending 10,000 gallons of water, glass, and wood crashing down to the silk counters on the ground floor. At the time, at least 3,000 people were inside the building, but only about 10 were injured, according to a New York Times account of the day.

“The vast crowd in the store was handled in a manner that resembled that in which the public school teachers handle their pupils in fire drills,” the paper wrote.

After the water tower disaster, Adams planned to merge the store with a competitor one block to the south. But the fashion world will chew you up and spit you out, and as the classier department stores moved north to Herald Square and Fifth Avenue, this department store shut its doors in 1907.

My favorite era may have been in the early 1920s, when it was a manufacturing plant for Hershey’s short-lived chewing gum venture.

According to the Bowery Boys: “Soon the Sixth Avenue shop was whirring with the sound of boilers, mixers, candy presses and wrapping machines, sending out five thousand boxes of chewing gum a day, and a lesser amount of other candy items. Wheat was carried in from the Pennsylvania plant and added to the gum to make it more chewy.”

Over the past century, the building has also been used as Army storage and offices for Mattel Toys, an ad agency, Fisher-Price and The Gap, writes a profile by the Flatiron NoMad Business Improvement District. When Barnes & Noble opened here in 1994, it helped spur the concentration of chains that now dominate the stretch, according to The Observer.

Now it’s Trader Joe’s store #543, and one of those locations where you may end up waiting in line as soon as you walk through the door. It’s not the most ornate TJ’s in New York City, but it’s still an imposing place to pick up some snacks. Anyway, if you’re heading that way, pick me up some dried mangoes and an orzo pasta salad, thx.

With the active bike lane, foot traffic, and occasional produce vendor, things can feel a little claustrophobic from time to time.

The dignified Italianate building, clad in Ohio stone, (the one with the Chipotle) was originally built as the Torrilhon House Hotel. Over the years, it’s housed dressmakers, embroiderers, and a china and glass merchant, according to the district’s landmarks filing.

A strange incident happened here in 1891. As Tom Miller at Daytonian in Manhattan tells it, the owner’s wife, Mrs. John Parke, spent a lot of time at her third-floor window watching the action on Sixth Avenue. One evening, she spotted two women wearing outfits she considered unacceptable and began yelling insults down at them.

In what the New York Times called an “ejaculatory period of unusual extent”² Mrs. Parke’s artificial teeth fell down to the sidewalk. The young women, maybe not inclined to hear more of these unkind words, walked off with the false teeth.

Mrs. Parke then took out an ad trying to retrieve them, which brought in a crowd of opportunists with teeth to sell. As Daytonian pulls from the New York Times: “The advertisement brought a score of persons with teeth to exchange for money, and as a result Mrs. Parke was in such a state of mind yesterday afternoon that she did not feel like discussing the matter.”

So, uh, watch your mouth out there or people will run off with your teeth and clown you for it. Lesson as old as time.

Bonus: A company called Wolf Paper & Twine occupied this building and there’s still a cool ad on the neighboring building at Number 678, which has been combined with the building next door. A cool website that surveys faded ads caught this one over the years from 1990 through 2002.

As high fashion moved here, hat and fur merchant W.M. Hall opened this eight-story neo-Renaissance loft building, according to Daytonian, who adds that along with the typical furs came even more troubling inventory like “natural dog robes,” “sealskin capes,” and “Siberian wolf robes.”

Yep, this place even sold Labrador Sable ear muffs. Thankfully, it lasted here only until 1903, according to Daytonian.

The building took a different turn in the 1960s, when the Latino theater company Asociación de Arte Latinoamericano operated a 74-seat theater in a loft here from 1966 to 1971, before moving uptown. It was also home to the Peace & Freedom party, which ran in opposition to the Vietnam War and as an informal headquarters of the presidential campaign of Black Panther Eldridge Cleaver, who’d recently been paroled.¹

Now it’s condos. Nothing unusual with that these days, except these come with a special bonus: rent profits from the retail store below are used to offset maintenance costs.

In 2026, that store is The $10 Shop, described by one website as a “chaotic discount shop where prices are a mystery until checkout” with “party dresses and random finds.”

Everyone loves a good random find. But glad these racks no longer sell dog coats. Dog coats. Come on.

This two-story building hasn’t always been Pinot and peeling paint.

Around 1980, nightlife impresario Lewis Friedman opened a queer bar and experimental venue called S.N.A.F.U. It hosted drag shows, early ska bands, and the Coachmen, which featured a pre-Sonic Youth Thurston Moore.

One regular performer was Ethyl Eichelberger, once described as “a big man who plays big women” such as characters like Klytemnestra and Minnie the Maid.

Warholian star Holly Woodlawn also performed here regularly. According to one website (and a French translation of her memoir), unable to hail a cab, she hitchhiked to the club, making her opening-night entrance on the back of a white pick-up truck. (There’s video of the evening, but it doesn’t include footage of the pickup pull-up, unfortunately.)

One-time bartender Bob Bozic describes adjusting his eyes to the dark space as he walked around in 1981 looking for a job: “Inside was as dingy as the outside. The large room was scattered with square, gray formica tables, surrounded by black vinyl-cushioned chairs. The walls were adorned with life-sized black-and-white nude photos of couples embracing—some male/female, but mostly male/male.”

A few preserved flyers survive the venue.

By the end of the decade, the space would become Lox Around the Clock, a Jewish-style deli and afterhours spot. Passing through the logo—”nine Plexiglas salmon spinning around a large clock”—you could order a sandwich named after neighborhood clubs. Like the Kamikaze, which for $7.50 came stacked with corned beef, pastrami, and chopped liver, New York Magazine wrote in 1986.³

Oh sure, some said the matzoh ball soup’s “overwhelming yellow color did not match the insipid flavor,” but the homemade challah and borscht seemed to satisfy. And where else are you going to grab a bite after a night at the Limelight? Or encounter whatever health code violation seems to be happening on this Halloween in 1990?

They won’t let you do that at Trader Joe’s.

What’s Good: Dried mangoes and seaweed snacks. The old bones of Ladies’ Mile.

What’s Not: The lines. The chains. THE DOG COATS.

Block Rating: 6/10