Much will depend on the person driving the horse, and what conditions the horse is driven in. Educated hands teach the horse more with each outing. Ring driving can teach a lot, but doesn’t have much variety in exposure to new things.
I don’t think 20 hours is much in time, for a solid driving horse. It is a step forward, but no place close to being a finished horse. Putting the horse into new settings, picnic drive, driving show, is really pushing a horse hard, with his 60 days training, plus 20-30 hours of other driving. He just doesn’t have the depth yet to be real reliable, with all that new stuff coming at him.
Pricestory gave other good suggestions for getting horse out and seeing new stuff.
Some animals APPEAR to be accepting, but they can then surprise you when they lose their nerve or react poorly to something they have seen before. Others show only forward learning, never have a problem with all they get to see.
Unless you have trained a number of animals, you may not be able to “read them” very well by body language. This means you may be asking horse things he is not comfortable with. He may not understand things WELL, that you have already done. This is where your trainer needs to come on a regular schedule to review horse knowledge, watch you and him in your driving work to see if he has holes that will cause problems. A trainer will have better educated eyes, see the signals horse gives, that may have you in a danger zone you don’t realize. Should have suggestions to improve skills, progress steps to move on with.
Not being critical, but it sounds like horse and drivers, need some lessons to allow you to improve communication, continue to develop your skills with the horse. Trainer eyes see lots that we miss, can pinpoint an issue very quickly to prevent it becoming a problem.
There is no time schedule in driving, where you can say that horse is “trained”. At our house, we say horse has a “good start” when he has been hitched and driven, at least a 100 times. He gets worked and tired, building his new body for driving. No 40 minute session and done each hitching! Lessons are 3-5 days a week, building on what he already has learned. Not just done weekends, or once a week. That is a fair amount of hours involved, along with the needed handling to prepare for hitching, to have on a horse. Certainly the horse HERE gets extra stuff like long-lining, maybe ridden as well, in among the driving sessions. We tend to really set high standards for our horses, want them totally dependable in all situations. ALL of our safety depends on ALL the horses being reliable. So for us, a year of work and new experiences, going out and about will get horse up to the “pretty dependable” rating.
We “home folks with outside jobs” can’t get in the time and miles that the Amish trainers do, so horses don’t advance as quickly in being totally unflappable, road safe beside the highway! For the Amish trained horse, he may be hitched every day of the 60 days with 5 or more miles under his feet each hitching. Like a riding horse who gets 2 or more hours under a saddle each day, learns more faster!
Sounds like you have a nice quiet horse with good basics. Now he just needs consistant time and work to develop driving skills and high level of tolerance to the weird things all driving horses seem to meet!