The iconic Flatiron Building anchors the Flatiron District at the intersection of two very famous thoroughfares, Broadway and Fifth Avenue. Architect D.H. Burnham’s wedge-shaped tower was a marvel when it opened in 1903 and it remains one of Manhattan’s most notable photo ops. The neighborhood gains a unique energy from its seat at the center of the island where several neighborhoods converge: Though the boundaries are under some dispute, most agree that the Flatiron District includes blocks from 14th Street to the high 20s between Sixth Avenue and Park Avenue South — walk south and you’re in Union Square, west to Chelsea, or east to Gramercy Park. The northern border merges with an up-and-coming area that’s increasingly known as NoMad (North of Madison Park). Originally developed as an alternative business district to Wall Street, the Flatiron’s canyon-like blocks had become a bit of a no-man’s land by the late 20th century. But spurred by residential and commercial developments and an influx of advertising agencies, publishers and internet startups, its cache has returned.
Take the N or R subway train to the 23rd Street station and you’ll emerge at the base of the Flatiron Building across the street from Madison Square Park. Established in 1847, Madison Square is one of the city’s oldest parks. Its rotating art installations and summertime roster of concerts, readings and food festivals also make it one of the city’s liveliest. On weekdays, children and their grownups flood the grassy lawns and playground, while office workers and older neighborhood residents lunch on the shaded benches. The opening of Eataly, celebrity chef Mario Batali’s wildly popular Italian market/high-end food court (at the park’s southwest corner), has done little to diminish the notoriously long line for burgers and fries at celebrity restaurateur Danny Meyer’s Shake Shack (at the park’s southeast corner). Suited expense-account types, meanwhile, make a beeline for the elegant Eleven Madison Park restaurant (mid-park, on the eastern edge).
The Flatiron District is not particularly known for its cultural venues, but you will find the Museum of Sex at 27th Street and the Theodore Roosevelt Birthplace National Historic Site on 20th Street. Shoppers, however, are spoiled for choice. Big-box stores hold sway over Sixth Avenue and many of the nation’s top clothing retailers have storefronts on Fifth Avenue. (Note that the very high-end stores of Fifth Avenue are further north, on the avenue’s Midtown blocks.) Off-avenue, you’ll find numerous local boutiques, coffee shops and specialty stores — including quite a few selling stationery or photography goods and services. Bars and nightclubs take advantage of the area’s business vibe and proximity to residential areas (there are fewer neighbors to disturb here). Cabs are plentiful and, most nights, the area remains lively with happy-hour crowds and club-goers. But be aware that some streets can feel dark and lonely after storeowners have closed up shop.