My kid's school has a parade and parish picnic when the school year is over.

I have been asked to tow the float which consists of a large trailer and about 60 kids sitting on it.

I would love to do it, but I am concerned about liability. Anybody have any experience with this?

I would call my insurance agent, but I don't want to raise and red flags...

 

I would ask the school to have you listed as "named insured" on their policy, for this one time event. It should not cost them any extra in premium, and it's something that can usually be handled with a phone call to the insurance carrier. Since you are doing them a favor, they should be willing to make the call.