Before you start riding your horse regularly on the trails in a group setting, evaluate his personality and abilities. Ask yourself these questions:
Does my horse like being in close proximity to other horses?
Is my horse calm on the trail?
If you have a horse that gets excited when you take him on trail alone, he may be more comfortable when riding in a group. He may also get even more excited having other horses around him, especially if some of those horses are nervous. If your horse does not have much experience riding with a group, be aware that he might be nervous and difficult to control. If you can, try to ride in small groups close to home first.
Is my horse fit for trail riding?
If you haven’t been trail riding at all, or have only done short rides on occasion, consider getting your horse in better shape before you start riding with a group. Find out what kind of terrain the group rides on, and the length and pace of their rides. Gradually condition your horse to this type of riding so he is able to handle a group ride without stressing his body and mind.