The Upper West Side is one of Manhattan’s most layered and cinematic neighborhoods, shaped by Gilded Age ambition, immigrant ingenuity, and a long tradition of attracting creative misfits. On this walking tour, you’ll trace how a sparsely populated stretch of farmland north of the city became home to some of New York’s most storied buildings, boldest personalities, and most enduring cultural institutions.

The tour starts at Columbus Circle, where a monument to Christopher Columbus – funded by Italian immigrant communities in the 1890s – marks the gateway to the Upper West Side. From there, you’ll head north along Broadway, past the Lincoln Center campus and its extraordinary concentration of performance venues, through the Artists’ Colony on West 67th Street, and along Central Park West past the Dakota and the San Remo.

Along the way, you’ll hear how the Metropolitan Opera was founded out of Gilded Age spite, why the Ansonia once kept live seals in its lobby fountain and a farm on its roof, and how the fictional gang wars of West Side Story were filmed among the rubble of a real neighborhood being demolished to build Lincoln Center. The tour ends at Zabar’s on Broadway, the legendary New York culinary institution that has been feeding the Upper West Side since 1934.