These Boots Are Made for Walking: It’s Peak Tour Season on UWS

There’s something afoot on the Upper West Side this weekend: several walking tours that promise to add thousands of steps for those who are counting. Each tour invites participants to explore, connect, and see the city from a new perspective—all on foot.

From May 1-3, New Yorkers are invited to step outside and explore the city’s history, culture and character through Jane’s Walk NYC 2026. This beloved annual festival transforms ordinary sidewalks into local history lore. With more than 200 free walks taking place across the city beginning this Friday, May 1^st at 9:00 a.m., the weekend offers a rare chance to see familiar streets through fresh eyes. Organized by the Municipal Art Society, Jane’s Walk is inspired by urbanist Jane Jacobs. Whether you’re a lifelong Upper West Sider or just passing through, join neighbors, historians, artists and storytellers to engage with the community, rain or shine!

Several events this weekend celebrate the rich culture of the UWS. A “Wild Woman’s Walk on the Upper West Side,” led by Nancy Funke, invites participants on a journey through some of the neighborhood’s beloved landmarks. The roughly one-mile walk on Friday, May 1^st at 11:00 a.m. brings attendees through Central Park, with stops at the American Museum of Natural History, Belvedere Castle, Shakespeare Garden, Bethesda Fountain, Strawberry Fields, and the Dakota. This easygoing walk blends nature, history and the literary spirit to shine a new light on the beauty of the Upper West Side.

Film lovers will enjoy “Nora Ephron’s Upper West Side,” a guided walk through the neighborhood stomping grounds and filming locations of the iconic writer-director. Led by Katie Orenstein, this walk explores Ephron’s work–from “You’ve Got Mail” to “When Harry Met Sally”–and its influence on the culture of the UWS. The mile-and-a-half walk on Saturday, May 2^nd at 11:00 a.m. is subway-accessible and takes a scenic stretch through Riverside Park, bringing participants into the vibrant life of the city. (The Saturday walk has already filled up, a testament to Ephron’s influence and legacy).

For those who are drawn to the neighborhood’s architecture, “Railroads, Renewal and Revival–The Evolution of Riverside South” takes a deeper look at the far West Side’s transformation. Led by August Celestin, this one-hour walk on Saturday, May 2^nd at 6:00 p.m. traces the area over a century of change. From the industrial rail yards to Robert Moses-era development, and into the modern skyline and its ongoing projects, this walk will leave you with newfound knowledge about some of the neighborhood’s most historic sites, some of which are unfamiliar even to longtime West Siders. Stops include the 69^th Street Transfer Bridge, the former ABC studio on West 66^th Street, the Trump Place building on Riverside Boulevard, Extell’s controversial “poor door,” and Waterline Square.