Central Park
Hands down the most classic walks in this city are through Central Park. With so many winding paths and places to discover, you could make a whole day of exploring. A straightforward path could take you from the southeast end starting by the Plaza Hotel, walking north on East Drive up to the tippy top at 110th Street and then come full circle back down on West Drive. You're guaranteed to walk by all the landmarks in the park on this route.
[Photo via @centralparknyc]