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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.

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.

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.

Founded in 1944 and now a branch of the State University of New York, the Fashion Institute of Technology is a prestigious school teaching art, fashion design, and marketing, and boasts famous alumni, including Calvin Klein, Norma Kamali, and David Chu. Students have the benefit of internships with New York’s leading stores and designers. Of greatest interest to the public is the gallery, which has changing exhibits, often from their collection of clothing and textiles.

Here, at the heart of the city’s wholesale flower district, you can hardly see the sidewalk for the masses of greenery, shrubs, and flowers. Manhattan’s largest concentration of shops selling houseplants, trees, blooming plants, and all manner of flowers, fresh, dried, and artificial can be found here; if you can’t find what you want, it probably doesn’t exist. The district extends along 6th Avenue roughly from 25th to 30th streets.

America’s oldest Episcopal seminary was founded in 1819. This campus was built around two quadrangles in the 1830s, on a site donated by Clement Moore, who taught at the seminary. The main building, added in 1960, includes a library with the largest collection of Latin Bibles in the world. There are lovely inner gardens (9th Avenue entrance).

The center of a rowdy theater district known as the Tenderloin in the 1870s and 80s, until it was reformed. The Manhattan Opera House was razed in 1901 to make way for Macy’s, and other stores soon followed. The clock on the island where Broadway meets 6th Avenue is all that is left of the building occupied by the New York Herald until 1921.

Former whaler R. H. Macy founded the store in 1858 on 6th Avenue and 14th Street; the red star logo was from his tattoo, a souvenir of sailing days. Innovations included pricing goods a few cents below a full dollar and offering a money-back guarantee. The store was sold in 1888 and moved to the present building.