I can appreciate what Cathy is saying but I have been a musician for over 40 years and have done many benefits where we just played a gig, took up a collections (like at a local bar) and turned the money over to the targeted charity. You can also host a private event and probably avoid the permitting process.

But to be sure, hosting any large public gathering (like a bike or 5K run) would require several different levels of permits on the city, county and/or state level. Insurance and security would also be issues.

I would venture that contacting the local ACS or ALA (American Lung Association) would be a good resource of what hoops have to be jumped through from a regulatory perspective.