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Midtown Manhattan

Midtown Manhattan

Flatiron District-Union Square

This neighborhood takes its name from one of the city’s first skyscrapers, which sits on a triangular island block at 23rd Street, Fifth Avenue, and Broadway. The area draws shoppers up and down lower Fifth Avenue with big name brands, but food is really the name of the game. It’s all around, with the Farmer’s Market and the huge Whole Foods on Union Square, Trader Joe’s just down 14th Street, and world class restaurants everywhere. Except for the university students residing in the countless NYU dorms scattered around, people tend to go rather than live here.

Chelsea

Although young families are slowly turning this gayborhood into another stroller county, Eighth Avenue between 14th and 23rd Street – Gay Boulevard or Gayth Avenue – still forms the epicenter of gay New York. Appearances are everything here, and the buffer, the better. Strut your pecs, beam your whitened teeth and yank up the attitude, and you’ll feel right at home.

Gramercy Park-Murray Hill-NoMad (North of Madison Square Park)

The city’s only remaining private park is the focal point of the swanky address that Oscar Wilde and Humphrey Bogart once called home, and that Julia Roberts and Karl Lagerfeld do today. Gramercy Park is opened to the public only on Christmas Eve; otherwise you must have the key to relax in its gardens behind the iron gates. No jogging. No feeding the birds. No Frisbees. The rest of the neighborhood without golden key access tend to be young urban professionals living in brownstones and nearby rental towers.

Hell’s Kitchen (Hellsea)

The proximity to Theatreland has always ensured a fair number of actors and other friends of Dorothy frequenting the bars in Hell’s Kitty, but with rents increasing in Chelsea, the boys have moved further uptown, too – and in ever-greater numbers. Young 401k-counting professionals, blue-collar workers, Latino families and gaggles of gay boys now make up this neighborhood, which offers a much more relaxed vibe than Chelsea. Head west of Eighth Avenue for bars, cute shops and decently priced restaurants; east lands you in tourist and chain restaurant hell.

Midtown

From street level, Midtown Manhattan can be an often-uninspiring sidewalk jungle. Best advice: look up. Some of New York’s tallest buildings and architectural wonders can be found in this neighborhood. Banks, media companies and ad agencies, and the skyscrapers that house them, are all here. Crowds of office workers file out of Grand Central Terminal every morning, coffee in hand, to start the daily grind in the Chrysler Building, the Empire State Building, and the United Nations headquarters, just to name a few. Tourists flock to the area to gawk at Times Square’s billboards and The Naked Cowboy, shop at the many made-for-tourists theme shops, or watch plays on Broadway.