I don't know which event or location they are discussing, but in many cases permits ARE required for an event. Ft. Desoto is one place where a permit is absolutely required for an -organized- public event. 20 guys showing up for a friendly race, no PA, no entry fees, no advertisers, etc are obviously not going to need a permit.
However, a permit may be needed at the starting, ending, or just the "party" location (if there is one), if there are advertisers, entree fees being collected, tents being set up, entertainment, equipment sales, or money changing hands, or a large group gathering, etc.
It really depends on the situation.
If there were an accident during such an event, the organizers would likely be held responsible. Waivers mean absolutely nothing, they should expect to get sued if someone's kid drowns when hit by a board during the race.
Entree fees or memberships are usually collected to help cover the cost of insurance, which offers some liability protection from these situations.
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