It's beautiful today - highs in the upper 40s with some wind, and nice and sunny. Pie and I got to go on a trail ride with Jill (of Buckskin and Bay) and Scout, and for part of the ride, Sugar and her owner. I already knew that Pie had rarely been ridden alone, and suspected that he might be anxious if another horse wasn't present, and in fact this proved to be the case. I rode him for a couple of minutes near the barn while the others were getting ready, and he wasn't too happy to be by himself, although he didn't do anything terrible. He's pretty attached to his new herdmates already, which I would have expected after coming to a new barn - they're his security in the middle of all the change he's experienced. So being by himself and herd-boundness will be something we will be working on over time.
I rode in Jill's Western saddle for security and Pie's familiarity, but ended up using a snaffle bit - he seemed not to like the curb bit I'd bought him.
Once the others came out, he was fine - he looked around quite a bit but was happy to head out down the trail. We were out for almost 2 hours, and except for one spook (more on that later) he was exceptionally well-behaved for such a young horse in a new place and seeing lots of things for the first time. With one exception, he just looked at things - I think having Scout along made a real difference, but now that he's seen a lot of new things, I think he'll be fine with them again without another horse (once we work through the herd-boundness). We saw many things, some of which I think he was seeing for the first time - people walking dogs, joggers, large boulders (he looked hard at these), suburban yards with yard furniture, barking dogs and other stuff, the farm areas with plastic row covers and chickens and turkeys, the community garden, busy roadways, a train and the train station, paved streets with different surfaces (the black asphalt was a little worrisome), striped road crossings, the square with shops and a large working fountain, a school with a large playground area and children's play equipment, construction barrels and road equipment along the road that's being widened, and bicycles. The only thing that caused him to actually move his feet in a spook was the bicycles - they approached from behind, and I turned him to face them as they passed by and he scooted sideways. I'm pretty certain that he's never seen a bicycle, much less one moving with a person on it. He calmed down quickly afterwards, but kept watching the bikes as they moved off into the distance.
I'd give him a A for trail manners in the company of other horses. He's happy to lead or to follow, will calmly trot to catch up when needed, and knows enough to pee on the trail when he needs to. I was pretty impressed. After we got back to the barn, Jill took Scout inside to untack and I rode Pie at a trot up on grass area behind the barn and we did some circles and figure eights at the trot - even though he was worried a bit about being by himself he was willing to do what I asked.
We'll have some things to work on, but we're starting from a pretty good place and he's a really nice horse!