Take a look at Jacob Ehn's blog post Automatically Merging Work Items in TFS 2010 . He wrote a plug in that can be downloaded from codeplex . It will automatically associate the work items that were associated with the merged changesets.
So when you merge to Main or Release the work items will be associated with the changesets in those branches, and the work items will be included in the build reports for builds off of those branches. The plug-in is super easy to deploy.
The other option is that you can build a custom workflow activity that you can run during your build that can traverse the merge history for each of the changesets that would normally be associated. It's essentially walking the tree starting with a known set of associated changesets. I would prefer this approach since you can let your developers worry about only needing to associate work items with the original changesets instead of having to also do it with merge changesets as well.
This also allows you to get around having to deploy a custom work item policy as Bryan described in his suggestion.
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