8 Best Sights in New York City, New York

Walk up a small and unassuming staircase from St. Nicholas Avenue in Washington Heights, and Sylvan Terrace appears as if you have magically stepped back in time to 19th-century New York City or onto a film set. The one-block cobblestone street lined on both sides with charmingly restored wooden town houses built in 1882 is one of New York City's greatest hidden streets/gems. Before the rows of town houses were built, the street served as a carriage drive to the 1765-built Morris-Jumel Mansion, the oldest house in New York City. The quaint town houses are occupied (and rarely come on the market, sorry) but are still worth visiting, especially when paired with a visit to the Morris-Jumel Mansion. A view of the mansion, framed by the charming yellow houses with ornate brown details and usually unobstructed by tourists, can be seen when looking eastward.

Walking the stretch of Bleecker Street between 7th Avenue and Broadway provides a smattering of just about everything synonymous with Greenwich Village these days: NYU buildings, record stores, Italian cafés and food shops, pizza and takeout joints, bars and nightclubs, and funky boutiques. A lazy afternoon here may consist of sampling some of the city's best pizza, grabbing an espresso, and soaking up the downtown fashion scene. Foodies love the blocks between 6th and 7th Avenues for the specialty purveyors like Murray's Cheese (No. 254). At the intersection of Bleecker and Carmine Streets is Our Lady of Pompeii Church, where Mother Cabrini, a naturalized Italian immigrant who became the first American citizen to be canonized, often prayed. West of 7th Avenue, the shops get more upscale, with fashion and home-furnishings boutiques featuring antiques, eyeglasses, handbags, shoes, and designer clothing.

The main thoroughfare of "Little Odessa" is where you'll find a Russian caviar boutique amid the Cyrillic shop signs advertising everything from pickled mushrooms to Armani handbags. When the weather's good, local bakeries sell sweet honey cake, cheese-stuffed vatrushki danishes, and chocolatey rugelach from sidewalk tables.

A curved, one-block lane lined with small row houses, Gay Street was probably named after an early landowner and definitely had nothing to do with gay rights. In the 1930s, this tiny thoroughfare and nearby Christopher Street became famous nationwide after Ruth McKenney began to publish somewhat zany autobiographical stories based on what happened when she and her sister moved to No. 14 from Ohio. The stories, first published in the New Yorker, birthed many adaptations, including the 1953 Broadway musical Wonderful Town and the 1942 and 1955 movies My Sister Eileen.

If you're looking for a good place to start your exploration of the Lower East Side, Orchard Street, from Houston all the way down to Canal Street, is probably the densest conglomeration of restaurants, cafés, boutiques, and art galleries. It's the perfect place to wander, checking out the art, browsing for clothes and knickknacks, stopping for a coffee or a glass of wine, and having a meal. Although no one gallery really stands out—you're best off visiting whatever catches your eye—look out for Perrotin ( 130 Orchard St.) and Krause Gallery ( 149 Orchard St.).

This narrow, gated cul-de-sac off West 10th Street between Greenwich and 6th Avenues has 10 diminutive 1848 row houses. Around the corner on 6th Avenue is a similar dead-end street, Milligan Place, with five small houses completed in 1852. The houses in both quiet enclaves were originally built for waiters who worked at 5th Avenue's high-society Brevoort Hotel, long since demolished. Later Patchin Place residents included writers Theodore Dreiser, E. E. Cummings, Jane Bowles, and Djuna Barnes. Milligan Place became popular among playwrights, including Eugene O'Neill.

Steeped in New York City history and shaded by graceful gingko trees, this somewhat-hard-to-find section of Leroy Street has 15 classic Italianate brownstone and brick town houses (1851–54). Novelist Theodore Dreiser wrote An American Tragedy at No. 16, and poet Marianne Moore resided at No. 14. (Robert De Niro later lived here for decades—in mid-2012 he sold it for $9.5 million.) The colorful (and corrupt) Mayor Jimmy Walker (first elected in 1926) lived at No. 6; the lampposts in front are "mayor's lamps," which were sometimes placed in front of the residences of New York mayors. This block is often used as a film location: No. 4 was the setting of the Audrey Hepburn thriller Wait Until Dark. Before 1890, the James J. Walker Park, on the south side of the street near Hudson, was a graveyard where, according to legend, the dauphin of France—the lost son of Louis XVI and Marie Antoinette—is buried.

Once the hub of the edgy East Village, St. Marks Place is the name given to idiosyncratic East 8th Street between 3rd Avenue and Avenue A. During the 1950s, beatniks Allen Ginsberg and Jack Kerouac lived in the area; the 1960s brought Bill Graham's Fillmore East (nearby, at 105 2nd Avenue) and the experimental Electric Circus nightclub (at Nos. 19–25 St. Marks), where the Velvet Underground and the Grateful Dead played. The shaved-head punk scene followed, and at No. 33, is where the punk store Manic Panic first foisted its lurid hair dyes on the world. At No. 57 stood the short-lived Club 57, which attracted such 1980s stalwarts as artist Keith Haring.

These days, there's not much cutting edge left. Some of the facades lead to luxury condos, and there are a number of global fast-food restaurants for ramen and dumplings. The block between 2nd and 3rd Avenues has turned into a bit of a global fast-food mecca, with boba tea shops and several Asian restaurants alongside stores selling cheap jewelry, smoking paraphernalia, and souvenir T-shirts. The cafés and bars from here over to Avenue A attract customers late into the night—thanks partly to lower drink prices.