For those in the great city of New York City, specifically the Upper West Side of Manhattan, and into running (ok, I just limited my global audience for this post!), I have an inspirational -- or at least not monotonous -- 5 1/3 mile run for you!
Half of the run is in Central Park and the other half along the Hudson River Greenway. I'm showing 74th Street and 108th Sreet as the two places to cross back and forth between the park- and water-side legs, but you can adjust your numbered blocks up and down to suit your starting point and still keep the run about 5 miles
And the elevation profile of the route involves some decent hillwork (ok, by Manhattan standards anyway!). A 333 feet elevation gain all in little-ol' Manhattan! Oh yeah!