Thanks for this post I haven't been out there yet although I thought that I would see if my son could do it at age 6, he's a good rider but hes never went off road. Were gonna try it out this week
Start him out on the Morris bridge (hole-in-fence) trails like main, grandpa, misery, washboard, and palmetto. thats what I did with my boy to get him used to off road trails. he took to it like a fish to water. I think he is a natural bike rider, we road 18 miles on the Suncoast trail only a week after his training wheels came off! Also, I dont know what kind of bike your son has, but I bought mine a full suspension Wal-mart special (20") to help with the roots. he rode his old bike once on the trails with no suspension and hated it, but now he loves it.