hahaha i did both... i drove him and myself to the trail and met another person there with there horse. it worked out pretty well except for my guy being a sweaty mess when we arrived :/ needed 2 towels to dry him... such a punk but he was a dream on the trail. just make sure your horse is desentized to alot before going. it saved us acouple of times where the person we met there, her horse spooks still and my guy would go on like nothing happened so we both helped each other out that day from trailer standing to trail riding.
good luck i hope you have as much luck as me :) but atleast meet someone there so that way you have someone to help in case you need it. my guy wouldn't load when we got back. he wanted to stay with everyone so having 1 other person makes a difference. :)