1) Travis isn't aboard. There are very few other crew members capable of playing the calliope who have the desire he has to play it, so if they were otherwise busy (there could have been a sailing party somewhere), they wouldn't necessarily have broken away to play the calliope, as Travis might.
2) Due to the narrowness of the channel there, the navigation crew may have requested it not be played so they could hear their communications better. However if this was the case, the calliope could have been played prior to departure for the locals.
3)Unfortunately the idea of entertaining/pleasing the locals on shore isn't high on the priority list of today's companies. Previous owners back in the day realized that new passengers might be gained via things like calliope concerts, boat tours, handing out brochures at landings and locks. That isn't in the business model today.
4) Crew may have changed from the upbound Redwing stop and someone less enamoured of calliope music may now be aboard.
5) The early departure caught the player by surprise and they couldn't make it up there in time.