My Mother was a member of Motor Maids in the 60's and 70's. Dad and she would ride to the AMA conventions every year regardless of location. Daytona one year from their home in Seattle area had the Long Distance Award until the couple from Alaska rode in!
Never made much sense to me to trailer a bike to a motorcycle event, either. The trailer people I have met for motorcycles, anyway, strike me as "posers," more interested in how they look than how they ride.
Now, to race, or to bring more than one bike to something like riding the "Dragon," it would make sense to bring what you would ride in a van or trailer. But for a true cyclist, adventure rider or scenery cruiser a trailer would just be not right.