Yes it is possible. You can install several startup projects in your solution (right-click the solution, go to the "Installing startup projects" section, select "Multiple startup projects") and specify the action for each project contained in the solution ("No", "Start" , "Starting without debugging"). If several projects are set to "Start", the debugger will connect to each at startup.
When you reach the breakpoint, you can see which process is used in the Debug toolbar (you may need to show it; some profiles hide this by default). It will show which process you are currently viewing, what thread you are in, and what frame frame you are in:

I believe the default behavior is that when one process is interrupted, the debugger interrupts them all. This way you can check the status of any attached process when it reaches one breakpoint.
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