My game plan for the stretch of Manhattan between Union Square and NoMad — Greenmarket mornings, the Flatiron Building, and Madison Square Park, then Gramercy taverns, Irving Place cocktails, and some of the city's best restaurants. These are the spo...
Map
I stand at the tip of the Flatiron Plaza for the classic photo of the newly unwrapped Flatiron Building after years under scaffolding.
Flatiron Building
I grab a bench in Madison Square Park to check out the latest public art installation with the Flatiron and Empire State Building views around me.
Madison Square Park
I get a ShackBurger and a concrete at the original ivy-covered kiosk in the park where the whole chain started.
Shake Shack Madison Square Park
I wander the Italian market for fresh pasta and cheese, then grab a pizza and a scoop of gelato before I leave.
Eataly - Flatiron
I shop the Greenmarket on Monday, Wednesday, Friday, or Saturday mornings for apples, cider donuts, and whatever's in season.
Union Square Greenmarket
I people-watch on the steps at the south end of Union Square, where there's always a chess game, a street performer, or a rally going on.
Union Square
I stroll the brownstone blocks around Gramercy Park and peek through the iron gates of the city's famous private key-only park.
Gramercy Park
I take the free ranger-led tour of the rebuilt brownstone where Teddy Roosevelt was born, full of original family furniture.
Theodore Roosevelt Birthplace National Historic Site
I go for the cheeky, surprisingly thoughtful rotating exhibits and stay open late on weekend nights.
Museum of Sex
I lose an hour browsing the famous 18 miles of new, used, and rare books and always leave with a Strand tote.
Strand Bookstore
I browse the multi-level flagship overlooking Union Square and check the calendar for author events and signings.
Barnes & Noble
I browse the gorgeous art, fashion, and design books under the chandeliers in what I think is New York's prettiest bookstore.
Rizzoli Bookstore
I wander the floors of rugs, lighting, and home decor at this Broadway flagship even when I'm not planning to buy anything.
abc carpet & home
I walk in for a seat in the front Tavern room for a seasonal lunch without needing a reservation.
Gramercy Tavern
I book Union Square Cafe for Danny Meyer's warm hospitality and a bowl of their pasta at the bar.
Union Square Cafe
I order the crab toast and the whole-wheat pizza at Jean-Georges' farm-to-table spot just off the Greenmarket.
abc kitchen
I save up for the tasting menu in the Art Deco dining room overlooking Madison Square Park for a once-a-year splurge.
Eleven Madison Park
I bring a group to The Smith for a lively brunch and the giant chocolate cake to share.
The Smith
I order the Butcher's Feast at COTE so the staff can grill the Prime beef right at the table.
COTE Flatiron
I book Enrique Olvera's contemporary Mexican spot for a special night out and always save room for dessert.
Cosme
I squeeze in at the counter for Spanish tapas and a glass of sherry at this tiny Irving Place favorite.
Casa Mono
I share mezze, the Brussels sprouts, and warm pita with friends at this big, buzzy Lebanese restaurant on Fifth Avenue.
ilili NoMad
I come every holiday season to see Rolf's over-the-top ceiling of ornaments and lights over a schnitzel and a beer.
Rolf's
I grab a slice of the chocolate babka every time I'm near Union Square, and a loaf for later.
Breads Bakery
I pick up a cinnamon or maple cruller and a coffee at Daily Provisions on my way through the neighborhood.
Daily Provisions
I get my latte at Irving Farm's original café on a quiet, tree-lined block of Irving Place.
Irving Farm Coffee
I have a pint at one of the oldest continuously operating bars in the city, where O. Henry supposedly wrote The Gift of the Magi.
Pete's Tavern
I grab a booth, a beer, and a burger at this wood-paneled 1890s saloon that hasn't changed in decades.
Old Town Bar
I meet friends for cocktails in the over-the-top Victorian decor at Lillie's off Union Square.
Lillie's Victorian Establishment
I book a table at this elegant cocktail parlor for a date night with thoughtful drinks.
Dear Irving on Broadway
I go up to 230 Fifth for a drink with a straight-on view of the Empire State Building, and the heated igloos in winter.
230 Fifth Rooftop Bar
I come for weekend brunch in the cozy country-style dining room on Irving Place.
