The Upper West Side isn’t trendy or hip. And that’s exactly what locals prize about this relaxed enclave, which feels much as it did 20 years ago. A palpable sense of community and continuity is bolstered by long-time neighborhood stalwarts like food emporium Zabar’s and performing arts center Symphony Space. In fact, some residents find so much to like about the Upper West Side that they rarely leave (one joked that she needed a guidebook when going to the East Side). When they do, however, express stops on the subway make commuting to Midtown or Lower Manhattan a snap.

The Upper West Side presents a choose-your-own-adventure in housing options: elegant townhomes; doorman high-rises; walk-ups with roof decks overlooking Riverside Park and the East River; and exclusive co-ops—liked the famed Dakota—lining Central Park West. Nightlife centers around low-key neighborhood bars and unpretentious restaurants. And with greenspace all around and cultural mainstays like the Museum of Natural History, there’s never a shortage of ways to spend your leisure time.