We are getting into the Middle Ages in Volume 2 of Story of the World. I have heard a lot of people feel like they can't use this program with middle schoolers, but I think with a little tweaking and creativity it is totally possible! We are using the Activity Guide that goes along with it, as well as the student pages and quizzes, but I am beefing it up with lots of hands-on activities, more advanced work and lots of living books and historical fiction from the period.
We do more advanced map work simply by using blank maps printed from Owl & Mouse Educational Software and then giving her the same directions as in the activity pages. This way she has to know where things are instead of just circling the pre-printed words. I also have her show me different routes and such on the larger blank world wall map - that we printed from the same site - so that I know that she is aware of the perspective of location.
I also supplement using a lot of videos and classroom resources from sites like the History Channel Study Guides. Most of the videos can be found through your local libraries, ordered online and some are even available streaming online.
We tend to skip most of the "coloring pages", but every once in a while we will come across something that catches her eye. Like this illumination pattern that demonstrates the monks incredible labors to reproduce books -