If you go to a satellite/map hybrid view of the area, you can see that Anabella and Stovall's are just a straight-ish walk up to PPH, and then just a bit beyond for DLH.
If you go from a Harbor hotel (like HoJo) to DLH, take a taxi. It's NOT worth the walk. If there were no race going on you could get up super early and go through the esplanade and up to DLH before security is there (the esplanade is not locked up when everything is closed, you can go through), but with races going on it wouldn't be that easy. Actually, remembering spectating for Star Wars 5K, security wasn't going that early, so you
could just walk in EARLY, and then they have a system that allows people to cross the race route as runners go between the parks. But still, it would be a pain. Take a taxi if you stay on Harbor before moving to DLH.
We didn't feel silly walking up to PPH. We felt hot, but not silly.
you didn't ask me, but...
I started slowly running again, with intervals, in mid 2012 while losing 85 lbs. (I've since gained back 20 and am working to lose 10 of those) Tower of Terror 10 miler October 2013. First Half marathon January 2014. Did 5 more in the 12 month period including that Half. In 2015, October, I did a 10K and Half challenge with Rock 'n Roll Vancouver, and it went much better than I thought it would. Please note that I do not train as much as I should, so I'm rather slow and I hurt more than I should. I did the 5K and 10K at Princess this year, and plan to do those plus the Half at princess '17.
If you look on rundisney.com there's a link for Training. There you will find links to training plans for all sorts of rundisney events, and Galloway (the walk/run guy) is the trainer for rundisney. Those give you free plans for training even for the challenges. Pretty cool.
Before they clear out the race stuff and set up for the day they could, actually. There was no security that I went through from Anabella to viewing the 5K from the DTD side of the esplanade, and I would bet it was the same on the Harbor side. And they have a system for people to cross the running paths periodically. But that's an early morning. And a bit of a pain.
I do recommend a cab. But walking *could* be possible.
Does it feel old? Hmm. We never used a stroller at home except for the dedicated jogger for jogging. The other stroller we had was specifically, and ONLY, for Disney. DS used that through the age of 5, because I'm not interested in slowing down (walking slowly HURTS my hips and always has), and I was highly sympathetic for sore legs.
You're from WA, I see? Where?