When I was a teen occasionally I would let the whole herd come with me... So I would be bareback on my Anglo-Arab mare and with me would be a QH gelding, a Mustang mare, and and old Shetland pony gelding. Added to that was at least three to six dogs as well as sometimes the two goats. We would go out for hours.
The pony would drive cars nuts... it was a one lane dirt road and any car that came up on us would be stopped for a full inspection of thier headlights. He would stand in front of the car until he had sniffed both headlights before getting out of the way, then off all of us would go!