Ride Solo. When I take a horse on the trail for the first time, I prefer to ride him out by myself so that it’s just the two of us.
When you get two or more horses on the trail, they have a tendency to want to race one another and get reactive. And, when you do ride your horse outside the first time, you want to give him a job to do and do a lot of cantering. Your goal is to put some miles under his feet. You don’t want to be held up by other riders who only want to walk. The slower you let a horse’s feet go, the more he’ll start looking for things to spook at. You want to give your horse a job and get him moving his feet. Remember something, sticky feet will get you into trouble every single time.
If you don’t feel comfortable riding out by yourself and would rather have someone ride with you, make sure it’s someone who is on a well-broke horse. They can ride their horse ahead of you, and your horse can follow. What you don’t want to do is take the horse out for his first time in a group of horses that are reactive and bad-behaved on the trail. Whatever attitude the other horses have is the same attitude your horse will develop. So if you’re not comfortable heading out by yourself, be sure you choose a partner with a quiet, safe and dependable horse that will act as a good role model for your horse.