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I feel bad about the way I feel about it, because I REally don't want to do it, as I'm not real fond of this kid.

Ok, first of all, don't feel bad at all. Just tell the mother that you don't feel this girl is ready for a trail ride. It's as simple as that. Maybe after a little more practice she'll be ready. It's completely different on the trail than it is in the arena. Do you think her seat is secure enough? That she can stay on? I used to run into pushy parents and whiney kids all the time, and used to deal with the same thing time and time again. If all else fails, make something up. You don't want to take the horse on the trail because he's footsore. Tell her the truth and say that the trail is hot and buggy, and she won't like it. Something.
Be firm. Remember, these are your horses. They aren't paying you, are they? If you don't want to do something, you don't have to. :-)
And as for the helmet/barrels thing. Don't feel afraid to sit down with the kid and gently but firmly remind her that yes, she has to wear a helmet no matter what, and no, she can't canter (lope, sorry) until you feel she's ready, etc. Go over the importance of helmet safety.
I truely hope that you don't think that I'm a cranky witch. That's the end of my rant on your behalf. :-)

I enjoyed your cranky rant:)

I think the kid will be fine on the trail. For one thing the horse is as solid as you will find. And two, she's not a bad rider for her experience, she's just not ready to lope on Rock because he has such a powerful take off being an old barrel horse. I just don't care for her:) But, (and I don't like this about myself), I have trouble telling people no. No, they don't pay to ride my horses. I met Heather at church and you could tell she really really wants to ride, alot. Interested in doing/learning things the correct way. She just didn't get to ride alot because of the expense. I understand that 100%. And she's just a good kid too, very quiet. When we started going to this church and she found out thru the grapevine that I had horses she came and talked to me everytime we were there. You could just see how much she wants a horse and how much she wants to ride. I had a very good horse standing here doing nothing because no one had the time or desire to ride him because we were all busy with other ones. But I hate to see a good horse wasted. I told her if her mother was willing to bring her out here she could ride him and I would run her home when we got done. Well the thing has kind of snowballed to where all the kids, 3 besides Heather, and mom all take turns now. Funny thing 2 of them don't even want too do it, but mom wanted all of them to try. Don't get me wrong, I like the mother and don't think she is deliberatly taking advantage, I really don't, she just doesn't understand about horses either:), if you know what I mean.

Becky