The WIPO has a new database called IP Outreach in Practice which contains "basic information and links to practical examples of interesting IP outreach initiatives."
It's quite an interesting collection and a great place to look for inspiration and ideas. You can search by category (IP creation, IP use and awareness, IP crime), format (tv program, curriculum material, newsletter, etc.). There's an advanced search for more complicated queries.
WIPO wants to continue building the collection. You can send examples of outreach materials or initiatives to email@example.com.