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 some legendary ones), grocery options, and three dozen other stores—mostly luxury brands. Broadway is the main commercial strip, cutting its way diagonally across the Upper West Side. Along its length, you’ll find stores selling all the necessities of daily life. Are you interested in local, independent alternatives? Head to Columbus and Amsterdam avenues. If you still happen to have disposable income that needs disposing of, those are the spots where you can shop for things like books, clothing, or handcrafted and sustainable gifts. However, say you need a pause from all the purchasing, plenty of neighborhood restaurants await as well.