Heather took Pie and Drifter on an outing yesterday, and I got a full report last evening. She had planned to do this with them as part of their exposure to new things and circumstances. Drifter will be doing more of this after Pie comes home this week.
The report was very good - they both did very well. Both boys loaded well into her two-horse straight-load trailer (she's done no loading work with them, but Drifter's trailer-loading issues seem to be falling away just as we suspected they might) and rode well next to one another. Her friend's place was about 10 minutes away. Each horse was able to stand quietly in the trailer while the other was loaded/unloaded. Each boy hung out in the round pen while she worked with the other one. She rode them in the outdoor, and there was a lot of stuff going on while she was working with them - multiple horses being ridden and a new horse that was running and bucking in his paddock. And at one point at the end of her ride on Pie and beginning of her ride on Drifter, a small pony was being ridden - neither boy was quite sure what to think of the pony at first - I've seen this in horses that haven't seen ponies, or sometimes loud-colored horses like pintos or Appaloosas, before - but both ignored the pony pretty quickly.
Pie was groomed and tacked tied to the trailer, and although he was a little nervous, he stood pretty well. She hand walked him around the arena for a few minutes and did some simple ground work. He was attentive to her within a few minutes and she had a very good ride on him. He noticed everything, including the running, bucking horse, but kept his main focus on her.
Drifter was pretty quiet while waiting in the round pen, but was playful for a few minutes while the other horse was running and bucking. She groomed and saddled Drifter ground-tied outside the arena and he stood pretty well, needing only a few reminders. She also hand-walked him around the arena and did a few minutes of lungeing before getting on. He came around really well, and her ride was also very good. He would occasionally get distracted by horses coming and going, but could come back to her quickly. His transitions were mostly smooth with only one or two "hops" into trot.
Both boys loaded well into the trailer for their ride back to Heather's. I'd call that a pretty good report!