Gramercy & the Flatiron: the squares of the grid
The wedge-shaped tower, the original Shake Shack, and the park you can only look into. This is a Claude-drafted route awaiting the editor's walk.

1. The Flatiron Building
Stand at the prow where Broadway and Fifth Avenue cross — the building is only six feet wide at the point. Daniel Burnham's 1902 tower, one of the city's first skyscrapers. Photograph it from the north end of Madison Square Park; that's the angle everyone wants.

2. Madison Square Park
The square the Flatiron faces. Lawns, a dog run, rotating sculpture commissions, and the original Shake Shack kiosk in the southeast corner — the queue is the landmark. Eat a burger on a bench with the skyline stacked behind you.

3. Eataly
The Italian food hall on the park's west side — counters, a butcher, a rooftop bar, fifty kinds of pasta. Walk through even if you don't buy; it's a stop in itself. Busy from late morning, so come early if you want room to look.

4. Gramercy Park
The city's last private park — locked, key-holders only, and you genuinely can only look in through the railings. That's the point: peer through the gates at the one green square New York keeps for itself. The surrounding townhouses are the 1840s left intact.

5. Irving Place to Union Square
Walk down Irving Place, a quiet brownstone run, toward the noise of Union Square. The contrast — locked-garden hush to open-square clamour — is the walk's hinge.

6. Union Square greenmarket
The square's north end holds the city's flagship greenmarket — upstate farmers, cheese, cider, cut flowers — on Mondays, Wednesdays, Fridays and Saturdays. Time the walk for one of those and end with apples; come another day and it's still the city's great crossroads, just without the stalls.

Gramercy & the Flatiron: the squares of the grid