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I want to organize a large-scale bike ride through the city of Chicago as a message for the Bernie Sanders campaign. We would just ride around the city wearing shirts, waving flags, wearing stickers, whatever, chanting BERNIE, just to get word about their and to show the amount of support he has. 

My question is, in organizing something like this where say there are potentially 500 people who are riding together, do I need to organize the city or anything special so we don't get shut down or something?

I've never done this before. Any tips?

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Apart from the bike issues and saying this with no political intent at all I think  you want to make sure the Sanders campaign wants you to do this and is in agreement. Even if  it is an independent thing you want to know they have no objection. You may also want to know whether they prefer to make it an official campaign ride and whether (as any candidate needs money) whether they want to have a fundraising aspect or whether they even want you to hold it at a time when he is in  town. It is one thing to have a handful of cyclists make their statement. I take it you envision something bigger than that. You want to make sure a large scale thing has their blessing or at least does not have their objection. Candidates can be burdened when individuals take action in their name. For example, if there was an accident, an incident etc on the ride you wouldn't want to burden the  candidate with your actions. You want to help him. Just a suggestion. 

Thanks. Yeah I've already hosted a few events in the city for the campaign and have been in touch with campaign officials about the stuff I'm planning.

Steve, this is brilliant. I'd like to help out, too. But please, let's not do this like any sort of Critical Mass thing. Imho, that group is counter productive. Civil disobedience has it's place, but not here and I think the Sander's organization would agree with that.

I'm down,,,,keep me posted.

I'm down as well

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