The Coolest Streets in New York City

Home to hipster-approved entertainment, destination dining, and the best photo op in New York City, DUMBO has become one of Brooklyn’s top attractions. More specifically, the neighborhood’s Washington Street is what’s bringing tourists and locals alike to the area to strike a pose against a flawlessly framed New York backdrop featuring the Manhattan Bridge and Empire State Building.

As the site of some of the first mixed-race and openly gay bars in the 1800s and the café where Bob Dylan penned ‘Blowin’ In The Wind’ in 1962, Greenwich Village’s Minetta Street has always been the talk of the town. In addition to its historical intrigue, the Minetta Street of today offers picturesque 19th-century architecture and a tranquil reprieve from the surrounding Village streets.

The Lower East Side of Manhattan is one of the city’s most historically rich areas. Nowhere is this more apparent than on Orchard Street, an LES staple regarded as the center of the neighborhood. Travel back in time as you take in the street’s iconic low-rise brick-faced buildings, fire escapes, the Lower East Side Tenement Museum, and its weekly sidewalk mall.

Man Ray, Miles Davis, and more recently, the casts of Broad Cityand Girlshave all granted St. Marks Place their stamp of approval (and some enviable cool cred in the process). Keeping the street’s cool factor alive today are lively street vendors, old-school eateries, and quirky businesses, such as a speakeasy hidden in a hot dog restaurant.

On Manhattan’s West 28th Street, New York City’s Flower District brings new meaning to the phrase “urban jungle.” This small plot between 6th and 7th Avenues bursts with orchids, roses, lilies, and plenty of photo ops ripe for your picking.

Queen of ’90s New York Meg Ryan strolled this Upper West Side street in the beloved film You’ve Got Mail. Kathleen Kelly would be pleased to know Riverside Drive remains largely the same. Head up to around 91st Street to explore pre-war townhouses, Riverside Park, and the elegant New York of yesteryear.

Guernsey Street feels less like a residential block in Brooklyn and more like something out of a fairy tale. Here, a tunnel of canopy trees shades pedestrians as they admire charming, colorful row houses on this Greenpoint getaway.

A shopping hub, Manhattan’s SoHo has become overrun with chain stores and tourists (and New Yorkers can’t decide which is worse)! Luckily, Crosby Street provides an ideal escape from both, along with independent boutiques, cafés, and businesses housed in pre-war buildings. It’s still SoHo, however, so Crosby Street surveyors can expect a few celebrity sightings as well.