Interesting thread.
My personal preference is trail running. I enjoy the scenery and varying terrain, I like the challenge. I naturally have a shorter, quicker stride when trail running. I'll also end up walking more. The trails by us go straight up and and down a series of sand dunes. I like to wear a shoe with a stiffer sole, good ankle support, and less ventilation (help keep sand out of the shoes). I know VFF's are popular, but I have screws in both my feet so I am hesitant about the barefoot running.
I'm a lot faster running on the road. But I am constantly correcting my running form. I want to have a longer stride. I like to do my interval and speed work on the road. I will run on the road in any type of weather except for a thunderstorm.
The dreadmill is appropriately named. Running on it feels unnatural to me. But I do enjoy doing a good, hard, uphill walk on the treadmill while catching up on my favorite TV shows.



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Running on the trail does require more balance, and ankle/calf strength, sort of like going (semi-)barefoot, except with bonus obstacles! The area I run hill repeats in has some sections of packed gravel/dirt on the sides that I really love running downhill in, it's so much more natural than downhill on pavement.
I only use the treadmill if it's really icy outside or I am traveling and not comfortable with running outdoors where I am.