|One of my favorite New York long runs (about 15 miles to where I live) is to take the 1 or 9 train (I live in Manhattan) to the last stop - Van Cortlandt park in the Bronx.
Then run up to 132nd St. and head up the hill (it's long!) to Riverdale. Work your way to the East side of the Parkway and run South. After a while you'll see an entrance to a walkway across the bridge to Manhattan (not many people know about this!).
Crossing the bridge, you'll get to the northern tip of Manhattan. From here you circle back behind/under the toll booths to paths that lead you down to the Hudson river.
After all of that hassle, you can now run along the Hudson all the way down to 72nd St. It's flat and scenic and nice. Okay, there are a couple of odd sections - you need to run along the railway tracks for a bit, you need to climb a fence, you go through the RiverBank State Park and run just next to the highway.
But, all in all it's a great run. And a lot more interesting than three laps around Central Park.
If you try this run, send me an email and let me know what you think!