Good question. I've ridden my dog on trails, a lot in the winter, seldom other times.
I have a cocker spaniel and he's very good. He won't leave me, won't chase after deer, won't chase after other riders (except in front of my house!). He runs in front of me or behind me, I prefer behind me as he slows and gets confused if there are any forks or turns and I get close to him. Any other bikers, I pull over and hold him as a courtesy. Problems I've encountered, riders coming up from behind that I don't see, riders up front coming around turns and don't see the dog through the shrubs/trees, and then most of the time the trails are so narrow I can't pull over let alone pull over and hold the dog. I'm more likely to run him in the winter or weekdays when the trails are less crowded. never evenings or weekends.
I think the cowbell is a great idea and I think I'll get one of those small bell strands and wrap the bell strand around his neck. If that doesn't work, then a cowbell it is.