There are a couple ways to get ShapeFiles into the Silverlight control. One of the easiest methods is to import your shape files into SQL 2008 using the app found here:
An alternative method is to create a ShapeFile reader to import your files. The following is a simple example of how to do this: http://www.c-sharpcorner.com/uploadfile/nschan/shapefile02252007134834pm/shapefile.asp
x I've take a similar approach in the past for application and this works out well but requires a lot more work initially.
For both methods you will likely need to support multiPolygons/multipolylines. For this take a look at this article:
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