I was in beautiful NYC over the last weekend and went for a run through Central Park with a friend. I had always wanted to do it but never had the chance because I really didn't get into running until I no longer traveled into the city.
We ran about 40 blocks up (to 102nd St.) and then circled back and ran down the Upper West Side (west side of the park). We stopped by the Dakota (where John Lennon died) and ran through Strawberry Fields and passed by Tavern on the Green, among other things.
The walking/running/biking trails were amazing and it really took you through a nice path with some decent hills and great scenery. After having gone to the city 30-40 times in my life, this was a nice first for me.
I ran it without music, as it would have been quite rude to run with someone while listening to music. I think we ran a bit further than what my ipod said, but that's been the trend of late.