While the first mansions were built on the Upper East Side a few years after the opening of Central Park in 1858, it took the Upper West Side longer to get going. (This was due largely to the fact that elevated train service wasn’t inaugurated until 1879.) When construction on the Dakota began in 1880, so the story goes, the developer embraced the ribbing that, given its remote location, it might as well be in the Dakota Territory. A construction boom followed, and the neighborhood today consists mostly of apartment buildings (on Broadway and the avenues) and rowhouses (on side streets) from the late 19th and early 20th centuries, with some recent additions. Columbia University provides much of the vitality of the neighborhood’s northern reaches, while Lincoln Center and the American Museum of Natural History are the leading cultural institutions farther south.

Given that the neighborhood is roughly 50 blocks long and four blocks wide, you’ll be able to find almost any culinary or shopping experience you may want. At the neighborhood’s southern end, the Shops at Columbus Circle includes several restaurants (including the legendary Per Se), Whole Foods, and three dozen other stores, mostly luxury brands. Broadway is the main commercial strip, cutting its way diagonally across the Upper West Side. You’ll find stores selling all the necessities of daily life along its length, from Home Depot to a Fairway that is almost a neighborhood institution. Head to Columbus and Amsterdam avenues if you are more interested in local, independent alternatives, with plenty of neighborhood restaurants waiting when you need a shopping break. Book Culture, Frank Stella (menswear), Magpie (handcrafted and sustainable gifts), and West Side Kids are a few favorites when you want to dispose of some disposable income.