So far my farthest run has been sixteen miles, which I did in New Jersey, along the Ocean City boardwalk. That boardwalk is 2.5 miles long (conveniently labeled with mileposts at quarter mile intervals), so I ran the length of it and back three times, with an extra half mile tacked on getting to and from the boardwalk from the place we were staying.
That was a different kind of feeling. I generally don't like to run past the same point too many times, because it's too tempting to give up early. But the boardwalk had the advantage of giving me lots to look at, and lots to dodge. Other runners, for starters -- we had a whole lane to ourselves down the center of the boardwalk, divided from the bicycle and "surrey" (a kind of pedal car contraption for tourists) lanes by painted white lines, with pedestrians on the outside... At least until the shops opened, at which point all lanes became pedestrian lanes. Bicycles veering into the running lane to pass added a level of interest and difficulty.
I checked out the animatronic gorilla at the the jungle themed putt-putt place, the carnival games, the water slides, the T-shirt slogans at the endless souvenir shops, and still there would be different things to look at on the next pass, the arcades, the ice cream cones, the amusement park rides. (It's a very kid-friendly boardwalk.) And, of course, the beach and the ocean.
Sixteen miles was no problem, but a later, shorter boardwalk run through a raging storm with wind driven sheets of rain left me cold, dripping, tired, and with a damaged iPod.
After that I had to miss a couple of days because there was no place to go from our next hotel, and since we went back to work as soon as we got back home, I had to miss my next long run. So for the one after that, I went only fifteen miles, along Chicago's lakefront.
Hardest. Run. Ever. Two miles into it, I was dying. Miserable, punishing, torture. Left me feeling sick afterwards, and sore for the next couple of days. Why? I have no idea. Maybe I didn't eat enough carbs.
Maybe it was the fact that I was listening to the Cubs take a pounding from the Cardinals the whole time. (But it's okay, we're still 27 games above .500 and leading the division by 4.5 games. Whoo! Go Cubbies!)
In any case, my next long run, this weekend, will be 17 miles. I'll probably build up to about 20 before starting to step them down again to save strength for the real marathon.