Oooo nasty! Its something I always worry about when towing.
It sounds as though your trailer has a narrow track - is it one of those folding jobs ?? Some details - with a picture or two - would be interesting.
I bought a two-bike trailer, where a single bike uses a central channel. It has a decent, wide track - but it has to be towed everywhere (where its invisible to the driver when empty
I hope the 'Bobber' is OK.
My avatar shows the late Len Rich in 1970 with the bike I now have - a 1958 Ariel VH