You have to get this one right.
For the first six years, the CHIditarod ran without any permits. We were emphatic about everyone obeying all laws (e.g. cart acquisition; staying on sidewalks, etc.), although we understood how little actual control we had. The reason it is a food drive is that we figured it would give us a cloak of respectability and be harder to shut down. C’mon, SHOPPING CARTS. A FOOD DRIVE. HUNGRY PEOPLE. HELPING PEOPLE. It became our narrative. It grew into something very real and very satisfying.
We also designed embroidered patches, and got some extras to hand to police. Police love patches and trade them at their shows. Note that this is true in the United States. In other parts of the world, it may cause alarm on the basis of security concerns.
A couple of years, we had the race started by nuns. One time, we got a local alderman to start the race. Boy, was he surprised when it came up that we had no permit! The police brought it up when they responded to reports of sudden gridlock on a Saturday morning. A police sergeant finally declared: “Yeah, you’re doing a good thing… but you’re doing it all wrong.” This has been our motto since that morning.
You may do much better if you can start out courting authorities with respect and signing on good allies. A sympathetic councilman or pastor might help out. The local grocery store might play with you (and even loan the carts in exchange for display rights). You will also want neighbors to know what is happening and why, especially around the start and finish lines.
This is a great event when it is well done, and that means no surprises for police, partners, or neighbors. Nobody wants to get yelled at on Monday morning, so don’t set them up for a fall.
Everyone loves good causes. Everyone loves fun. For many of your neighbors, this may be their introduction to your community. Don’t just DO IT. DO IT RIGHT.