Taking a young horse from the arena to the trail for the very first time is exciting. There is a lot of anxiety involved. Will my horse love the lack of boundaries so much that he will just take off and run? Will he stay on the trail when I ask him to or will he want to veer out into the woods? Will he spook at everything he sees for the first time? And what about all the distractions on the trail? Will he be good or will he give me a hard time?
Your horse should be trained enough to follow commands before taking him out on the trail, and you should be able to control him. Practice riding him in walk, trot and canter in the arena and other enclosed areas. A good stepping stone between arena and trail is a large confined property with varied terrain, where you can practice going up and downhill and over and around obstacles. Practice your emergency stops by running the horse and then stopping him. It will come in handy if he indeed wants to run away from an imagined monster on the trail.
It is unlikely that your horse will try to run away with you, but it is quite possible that he will spook at the most unlikely things such as tree stumps, benches, pedestrians, and mountain bikers who will try out the horse trail even if they are not allowed there. You can take your horse on a practice ranch set up with obstacle courses for desensitizing.
One thing not to forget is to teach your horse to load in a trailer. It would be too bad if he would refuse to be transported on the day that you have been waiting for so long. For some horses it will not take long, but others need many tries and lots of patience until they go in easily. If you have no practice with training a horse to do this, you’ll need to find someone experienced to help you.
When you arrive at your destination with your trailer, take your horse out and lead him around. If there is space, lunge him before saddling and ride around in the vicinity of the trailer before joining others on the trail. You should not go alone but ride with experienced trail riders and horses, Their calmness will keep your mount calm and in-line. Happy trails!