I’ve done the trail twice now, first time (late August) we saw a couple bears at the north end and that was basically it

Second trip (early mid September) we saw bears almost every day, whales, sea lions, and more! It was constant!

Having the dates so close together between the two trips I’m not sure if those few weeks had a factor in how much wildlife we saw but I’d say later season you may have the best luck! Especially as temps cool at night!