Centered around Manhattan's sole remaining private park, Gramercy is a stunning enclave of 19th-century brownstones, surrounded by elite clubs and cozy bars and restaurants. It's an intimate neighborhood, where even the large, lively venues are appealingly personable: the lobby bars of Ian Schrager's recently redesigned Gramercy Park Hotel, frequently packed with celebrities, movie magnates and publishing impresarios for industry parties, maintain a rustic warmth (aided by the fireplace and smell of crackling pine); and the Fillmore East at Irving Plaza, a historic concert hall with room for 1,200, always manages to feel like a small club, which is perhaps why stadium giants like U2 continue to play special, one-off shows in the space. And while the area might be rife with artisanal contemporary cuisine and avant-garde performances, Gramercy Park's past is everywhere, too—from the City's oldest continually operating bar (Pete's Tavern, the place O. Henry made famous!) to the gorgeous fin-de-siècle buildings where Oscar Wilde, Margaret Hamilton, James Cagney and countless other legends lived and worked.

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