The Flatiron District takes its name after the famous Flatiron Building—né Fuller—at 23rd Street and Broadway, which creates such a wind-tunnel effect that it is said to have been the reason why "23 skiddoo" entered American slang, for the phrase cops would shout at men waiting around, hoping the wind would whip up a skirt or two. The neighborhood is bounded on the south by Union Square, a more modern gathering place for thrill-seeking goofballs and gawkers. Despite its questionable bounding buildings, the neighborhood is a fairly staid one, home to an eclectic mix of residents and businesses, many of which are publishers and advertising agencies.
On the northern edge of this neighborhood lies historic and recently renovated Madison Square Park on 6.2 acres between 23rd and 26th Streets and Fifth and Madison avenues. Madison Square Park
is one of two vibrant parks in the Flatiron district, as well as an oasis for those who live and work nearby. The park now features an expanded southeast corner, lush lawns and flowering plants, a restored 19th fountain, a contemporary reflecting pool, new benches, and ornamental lighting. The park is also host to Danny Meyer’s original Shake Shack
, an extremely popular lunchtime destination due to its top-rated burgers and thick shakes (although literally any other location of the brand will have a shorter line), as well as Eleven Madison Square
(formerly owned by Meyer) on the eastern side of the park, serving up some of New York's best upscale fare and ambiance.
On the southern edge of this neighborhood lies Union Square Park
, between 14th and 19th Streets and Park Avenue and Broadway. Some consider the Union Square area a neighborhood unto itself, as the immediate surroundings are a thriving cultural, business and education hub. The area is known for its top-notch restaurants, diverse retailers, off-Broadway theaters, excellent universities, teaching hospitals and, of course, Union Square Park, one of the city's most popular gathering points. Host to the first Labor Day Parade in 1882, the park continues to be used as the staging ground for numerous historic rallies and demonstrations. The park also contains a playground for the kids and a dog run for Fido so both can stretch their legs a bit and play alongside the city’s other often pent-up pooches. A popular sport here is bench-sitting, wherein you people-watch the diverse crowd of artists, college kids and skater dudes who flip their skateboards along the park steps near 14th Street.
Union Square also hosts a popular greenmarket, where more than 70 farmers sell fresh produce, baked goods and more every Monday, Wednesday, Friday and Saturday. During the holiday season, the southern end of the Park becomes the Union Square Holiday Market where dozens of vendors sell unique wears perfect for the gift-giving season. Surrounding the park, you'll find the stellar Union Square Barnes & Noble
, which hosts some of the world's top authors for readings and signings, a huge Whole Foods Market
, with self-catering dining options on the upper level, the requisite Best Buy
, and plenty of other shops. And given the nearby Regal Union Square 14
, we can call Union Square what it ultimately has become: the world's largest and least cohesive outdoor mall (complete with skate punks!).
If you find yourself getting hungry while perusing the greenmarket, there are plenty of restaurants in the area to satiate your appetite. Eisenberg Sandwich Shop
is one of New York's true gems and one of the few remaining, old-school luncheonettes. Enter the narrow doorway and grab a stool along the lengthy countertop and enjoy heaps of potato salad and pastrami on rye. For dinner hit up the Heartland Brewery & Chophouse
in Union Square, a spot that's known for its vast selection of burgers and homebrewed beers. And then there's Craft
, where you can enjoy gourmet cuisine by five-star chef Tom Colicchio, which now features a very special meal
every other Tuesday. While it's definitely on the pricey side (dinner starts at $150 a plate), it's assuredly worth treating yourself.
In terms of hotel accommodations, there are several options in the Flatiron/Union Square area. The W New York Union Square
is a stylish, deluxe hotel that's been named one of the "Top 500 Hotels in the World" by Condé Nast Traveler. For the more budget-conscious traveler, there's the charming Union Square Inn
and the Hotel at Madison Park