I ride with my dog regularly. When we started it was always on leash but I kept a loose hold on the leash, if he pulled hard or stopped short I would simply let go to avoid crashing and scold him. He is now trained to ride next to my rear wheel, to my right. I can let him off leash if it's late and there's nobody around to care, or on leash.
Our rides are normally 2-6 miles with 1 mile on the road and up to 5 off road. I'm sure he's capable of more, but he can be alot of trouble so I leave him at home on longer rides. I'm not sure I can recommend long road rides with a dog.
As well trained as he is, he caused me to wreck on Sunday. I was pulling my daughter on a trailercycle with the dog on a leash. He got startled by another dog and stopped short causing us to go down. Every one was ok with a few scrapes and bruises, but it was not a pleasant experience for my 5 year old. I will still continue to ride with him, but I will leave the dog at home when I have the kids in tow. I don't mind a crash now and then but my little kids do.
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