SaddleSore

So far my 'little' one and I have never ridden out on a trail, just clear and flat ground. I am interested in trying, as a change of scene for both of us, but what preparations would I need to take? Is there anything in particular I should be aware of?

purplefdu

You need to be aware of everything. Even things your horse isn't afraid of in the ring or pasture or barn may suddenly become terrifying on the road. Sounding out the horse by yourself ahead of time and making sure it is capable of being controlled by the little one or "ponied" by you for control is a good start. Long sleeves, pants, boots, gloves and a hard hat will keep the child safest should they come off. Stick to well groomed trails or lanes without traffic or distractions.

showboat

My biggest concern would be a child on the trail for the first time. Purple has given some excellent suggestions on proper protective clothing which should definitely be followed. Another concern would be the distractions found on the trail as well as occasional obstacles like low hanging branches or fallen limbs. You will need to be prepared for unexpected things like this even on a well cared for trail and you need to make sure your child is as prepared as possible, too.