It happened when I was in middle school. I used to live in a neighborhood that was directly next to a large orange orchard that went on for miles. There was one main road that that split the neighborhood from the orchards.
During some weekdays my friends would go over to each others homes. This day we went to my friend's house who lived the farthest away from us, it was about 2-3 miles from my home. I lived the closest to "civilization" and would walk 5 blocks to pick up a friend to go over to my other friends home.
As we made our way over we decided to take an alternative route through the orange orchards. We made that decision because some people would leave their gates open and their dogs loose, we had close calls before and didn't want to risk it. We would walk in the areas where trucks and tractors drive through during harvest season, because it's the most open area about the size of a typical 2 way street but we were surrounded by dense orchards. We walked over to my friends home and played games/hung out.
We lost track of time and suddenly realized that it started getting dark out. Since we didn't want to walk back in pitch darkness me and my buddy decided to walk back asap. We decided to walk back through the same route we came through to avoid those aggressive dogs. After about a mile of walking and talking I stopped mid sentence because I had some weird sense to look back behind us. My eyes must have opened up wide enough that my friend also looked back. We saw this 7-9 foot shadowy figure that seemed to be facing us, and I just remember everything was completely silent. I couldn't really tell because by this time it was too dark to make out any detail. We didn't run we just started walking faster. Since the ground wasn't completely flat I almost tripped since I had my eyes locked on that thing. The moment it took me to look forward, regain my balance and look back the shadowy figure got significant closer. From about 1 mile away to about half a mile, then maybe 1000 feet wtf is this thing. My friend was completely still and I had to grab his forearm and start running. We ran as fast as possible back to the main road and continued running towards his house.
I don't believe in the paranormal but this is the creepiest / weirdest thing that i've ever experienced. The thing is that we both saw it which makes it creepier.