Once i killed a pronghorn at an estimated 600 yard. That is my longest shot ever. The goat next to it just kept grazing when the dead one fell; so far away it had no idea us white men were shooting at them i guess. It was so far, the boys wouldn't let me go out and gut it.
My muzzle loader max is 250 yard for 50 caliber, and 1/4 mile for 45 caliber.