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Chelsea and Herald Square : Overview & Top 10

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A neighborhood that has seen a great deal of recent change, Chelsea was a quiet enclave of 19th-century brownstones that never made it as a fashionable address. Now it is a hub for gay New Yorkers and center for the city’s avant-garde art galleries. Buildings along 6th Avenue are now occupied by superstores and discount outlets, and to the west, Chelsea Piers has transformed the waterfront. Uptown, the Garment District begins around 27th Street, with Herald Square and Macy’s at the heart of the city’s busiest shopping area.

  • Featuring artists of critical acclaim in several media.

  • Anchored by Macy’s, which opened in 1858, this was once a popular district known as “Fashion Row”. The 1876 cast-iron façade of the Hugh O’Neill Dry Goods Store at Nos. 655–71 exemplifies the era, when the arrival of the 6th Avenue elevated line provided easy access to the area. As Manhattan’s commercial center moved northward, these cast-iron palaces were left deserted until recently, when they found new life as bargain fashion outlets and superstores.

  • Morning

    Wind your way through Chelsea, starting with the megastores now occupying former “Fashion Row,” on 6th Avenue (see 6th Avenue Shopping) between 18th and 23rd streets. Walk west on 16th Street to 9th Avenue and Chelsea Market, a one-time Nabisco factory where the first Oreo cookies were made, now a block-long line of stalls offering all manner of food. The Food Network tapes its TV shows in a street-level studio here.

    Continue up 9th Avenue to 20th Street, for the Chelsea Historic District and General Theological Seminary. Then head for the ever-expanding “Gallery Row,” from 21st to 24th streets, 10th to 11th avenues. A good lunch bet in the neighborhood is The Red Cat , offering Mediterranean fare.

    Afternoon

    Walk east on 23rd Street to the Chelsea Hotel (see Chelsea Hotel), and when you get to 6th Avenue, turn uptown for the big antiques market and the colorful Flower District . A stroll for one block further west on 27th brings you to the Fashion Institute of Technology, where the gallery usually has interesting displays.

    Head for one of the great hidden treasures in this area, St. John the Baptist Church, at 210 East 31st Street, whose dingy façade belies a glowing Gothic interior. Continue to 34th Street for Herald Square and Macy’s.

  • Since moving from SoHo to Chelsea, Rosen’s eclectic shows have made this one of the area’s most visited galleries.

  • On weekends, year-round, an empty parking lot becomes one of the city’s most popular outdoor markets. A tradition for more than 30 years, some 600 dealers, from Maine to Maryland, set up booths selling clothing, silver, jewelry, furniture, art, and “junktiques” from old tools to vintage eyeglasses. Many prize antiques can be discovered at The Amex, an indoor market just around the corner at 112 West 25th Street, and at The Showplace, 40 West 26th Street, with 135 dealers on three floors.

  • A dramatic backdrop for large-scale pieces, video pioneers, and photography.

  • Thanks to the booming gallery scene, this attracts a stylish crowd for good northern Italian fare and a lovely garden.

  • A romantic bit of Paris in Chelsea, with a candlelit terrace and sophisticated bistro menu.

  • Clement Moore, author of A Visit from St. Nicholas , developed this land in the 1830s. The finest of the townhouses built here are the seven known as “Cushman Row,” Nos. 406–18 West 20th Street, which are among the city’s best examples of Greek Revival architecture. Houses at Nos. 446–50 West 20th are in the Italianate style, for which Chelsea is also known.

  • Seedy it is, yet there’s a definite mystique to this 1884 building bedecked with wrought-iron balconies. Once a fancy apartment, it became a hotel favored by musicians, artists, and writers. Former guests, commemorated on brass plaques outside, include Tennessee Williams, Mark Twain, Jack Kerouac, and Brendan Behan. Dylan Thomas spent his last years here. Notoriously, it was also the place where punk rocker Sid Vicious killed his girlfriend Nancy Spungeon in 1978. Step into the lobby and take a look at the wild artwork, and soak up the ambience at the bar.

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