I find this to be a very interesting question. I'm going to think out loud here a moment...
Ultimately, what we are faced with is a decision to violate a design-pattern acceptable practice in order to achieve a specific set of functionality. So, we must ask ourselves
1) What are the possible solutions that would not violate MVC pattern
2) What are the possible solutions that would violate the MVC pattern
3) Which option is best? I consider design patterns and standard practices very important, but at the same time if holding to them makes your code more complex, then the right solution may very well be to violate the practice. Some people might disagree with me on that.
Lets consider #1 first.
Off the top of my head, I would think of the following possible solutions
A) If you are really interested in who is performing these actions, should this data be stored in the model any way? It would make this information available to your Observer. And it also means that any other front-end caller of your ActiveRecord class gets the same functionality.
B) If you are not really interested in understanding who created a entry, but more interested in logging the web actions themselves, then you might consider "observing" the controller actions. It's been some time since I've poked around Rails source, so I'm not sure who their ActiveRecord::Observer "observes" the model, but you might be able to adapt it to a controller observer. In this sense, you aren't observing the model anymore, and it makes sense to make session and other controller type data information to that observer.
C) The simplest solution, with the least "structure", is to simply drop your logging code at the end of your action methods that you're watching.
Consider option #2 now, breaking MVC practices.
A) As you propose, you could find the means to getting your model Observer to have access to the Session data. You've coupled your model to your business logic.
B) Can't think of any others here :)
My personal inclination, without knowing anymore details about your project, is either 1A, if I want to attach people to records, or 1C if there are only a few places where I'm interested in doing this. If you are really wanting a robust logging solution for all your controllers and actions, you might consider 1B.
Having your model observer find session data is a bit "stinky", and would likely break if you tried to use your model in any other project/situation/context.