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Just putting up posters and advertising in left-wing media doesn't do it anymore. You get the same 500 people each time.
The people organizing these marches need to first create links with any and every organization in their community that could possibly be opposed to this war and ask for that group to select a liaison and set up a phone or e-mail tree. These groups in turn may know of more obscure groups that share their sympathies.
When a demonstration is planned, phone or e-mail the liaisons and have each liaison spread the word in his/her group, urging group members to show up and bring a friend. If the group member hesitates, have the liaison ask what the problem is. If the person has to work, ask if they can get off. If they don't have transportation, find someone who will take them. If they have child care issues, assure them that children are welcome. Etc. etc.
Choose a spot that is highly visible and centralized. If I were staging a demonstration in Minneapolis, for example, I wouldn't choose Uptown or Lake and Hiawatha, which are just neighborhood centers, but the Nicollet Mall in the heart of downtown, preferably in front of one of the large banks. Marchers would pass out buttons to passersby who expressed support.
The typical pattern is a march followed by hours and hours of speech-makers telling the marchers stuff they already know.
Put the speechifying at the BEGINNING of the march and keep it to no more than 10 minutes unless there is specific NEW information to be shared.
Or try something other than a march. To use a Minneapolis example again, recruit people to stand holding hands (or standing a few feet apart holding signs) down the entire length of a major street.
(Years ago in the Portland area, the fundie churches did this for an anti-choice rally, standing with signs along a major street, and it was creepy but impressive. It made their numbers look larger than they really were.)
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