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Gramercy and Madison Square Parks: NYC Walking Tour

This leafy New York City neighborhood brims with landmark architecture, historic sites, and more recently, good eats.

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Rating: 5 out of 5 by EveryTrail members
Difficulty: Easy
Duration: Unknown
Family Friendly

Overview :  Wedged between Midtown’s grandeur and the grittier East Village is a nexus of elegant and historic neighborhoods—Flatiron, Gramercy, “... more »

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Points of Interest

Some buildings are born to be icons. With its unique triangular “iron” shape, Beaux-Arts styling and bragging rights as one of New York’s first skyscrapers, The Flatiron Building’s eternal fame was secured from the beginning. Built in 1902 by Chicago-based architect Daniel Burnham, it stands 22 stories tall at the multi-street intersection of... More

In 1909, the Metropolitan Insurance Company had outgrown its 11-story headquarters. To solve its spatial issues, it added a tower—The Met Life Tower—to the existing building and became an instant landmark. The Met Life Tower held the title of World’s Tallest Hotel for three years, from 1909 to 1913 when it was unseated by the Woolworth Building.... More

3. 69th Regiment Armory

Designed by architecture firm Hunt & Hunt, New York City’s 69th Regiment Armory was the first to trade medieval design for Beaux-Arts style. Construction of the landmark on Lexington Avenue and 25th Street began in 1904. Aside from housing the 69th Infantry Regiment, which it does to this day, the building became famous in 1913 after hosting... More

Teddy Roosevelt, born on this site (this townhouse is actually a replica of the one he lived in until he was 14), grew from a frail child to a burly and energetic reformer, soldier, outdoorsman, and, of course, U.S. president. Lovely period rooms, furnished with items from the original home, show the lifestyle of a well-to-do family in the 1860s.... More

Two of New York’s major boulevards, Broadway and Fifth Avenue, converge at Madison Square, where seven green acres encourage you to pause to savor views of the iconic Flatiron and Met Life buildings—and burgers at Danny Meyer’s Shake Shack. Named for former U.S. president James Madison, the park officially opened in 1847, as wealthy locals moved... More

6. Peter Cooper

Peter Cooper (1791–1883) was one of the richest NYC residents during his time, but lived a rather modest life, considering his vast wealth. He is best known for designing and building the first U.S. steam locomotive; manufacturing iron; investing in real estate; and being the oldest person (85 years) to be nominated for President. Though his home ... More

The longtime object of envy, exclusive Gramercy Park is the only private (read: locked) park in New York City, open to only dues-paying key-holders, whose tony townhouse residences ring the Victorian green space. To many, its history is more accessible (and more interesting) than its present incarnation: Named "Crooked Little Knife" in Dutch, or “... More

Sure, Danny Meyer has his multi-award-winning fine-dining establishments, but his fans' most unabashed adoration has been reserved for his contemporary, urban rendition of the roadside pit stop. Shake Shack is an ode to two of his most beloved St. Louis locales—Ted Drewes, of frozen custard fame, and Steak 'n Shake, a burger (predominantly) and... More

9. Eataly

New York’s Eataly—a vast emporium dedicated to all things Italian and delicious—gathers a transatlantic all-star team of pizzaioli, gelato-makers, brewers, bakers, wine experts, pasta artisans, and celebrity chef, Mario Batali. With seven restaurants and a marketplace selling everything from salumi and Sicilian amaro to kitchen tools and cookbooks... More

Beloved for its cozy tavernlike charm (think wooden beams and twiggy flower arrangements), creative cocktails, and the seductive aromas that waft from the open grill, this New York institution is just one reason for Danny Meyer’s fan base (Union Square Café and The Modern have only enhanced his mystique). And thanks to chef Michael Anthony,... More

From Danny Meyer’s Union Square Hospitality Group comes Maialino, a neighborhood Roman trattoria overlooking Gramercy Park. The restaurant’s enoteca is an ideal place for a pre-dinner glass of wine and a small bite to eat. At the long wooden bar, patrons can order from the all-Italian wine list, which offers selections by the glass, quartino, and ... More

When design partners Ian Schrager and Julian Schnabel unveiled their reimagined, ultraswanky Gramercy Park Hotel in winter 2006, it brought modern glamour back to this 1925-era property. The 185 rooms—done up in Raphaelite tones of jade, claret, and sapphire blue—have chairs and ottomans upholstered in thick velvet, studded leather hope chests,... More