You might check to see if there is a riding club in your area. We belong to a trail group. We often have people who bring horses out just to get them used to trail riding with a group of seasoned horses.
Its fun to belong to a club too
Id never ride my horses alone the trails, If the trails went to the back of my house instead of having to ride about a mile down to get on, I would consider going by myself but it does get very lonely when im use to going out with my freinds.