The Upper West Side: Unconventional, Iconic and Wonderful

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.

On this 120-minute tour, you'll have a chance to:

• Discover the tragic story of Audrey Munson, America's first supermodel, whose likeness appears twice at the USS Maine National Monument
• Explore Lincoln Center's grand plaza, surrounded by the Metropolitan Opera House, David H. Koch Theater, and David Geffen Hall
• Admire the Dorilton's exuberant Second Empire façade, which critics once called so loud it could frighten weak women
• Hear how the Ansonia attracted Babe Ruth, Igor Stravinsky, Arturo Toscanini and Bette Midler – at very different points in its history
• Stop at the legendary Dakota, where John Lennon lived and died, and where celebrities including Madonna and Cher were turned away by the co-op board
• Pass the American Museum of Natural History, home to 32 million artifacts across more than twenty interconnected buildings
• Spot the ghost sign for the J. M. Horton Ice Cream Company, once the largest ice cream manufacturer in the world, visible from the old Ninth Avenue Elevated Railway

Whether you're a first-time visitor or a longtime New Yorker, this tour will leave you with a richer sense of the neighborhood's character – and possibly a strong craving for smoked fish.

CREDIT: Most of the music accompanying this tour is from the Frank Sinatra tribute album, From Hoboken with Love, by David Zaks Trio.