Since no one else has responded I will, even though I have a middle schooler. Generally, Madison is ok. Moving here was a HUGE adjustment for my child because we've lived in two very large cities, so this was a major slow down.

Good:

What's good about Madison, is that, even though it's ridiculously small, there are a lot of activities for children K-8. It is generally a safe place, and, if your child is in the right school, can get a world class education. Similar to a large city such as NYC, my child has friends who were born on every continent, and he has learned about various cultures. His school is phenomenal, and has superior core curricular, co-curricular, and extra curricular activities. There are also several community programs in which he can engage. For my husband and I, the small size of Madison is very convenient, so we can get to almost anywhere we need to be in 20 minutes or less, so taking our child to various program activities is convenient.

Bad:

There's not a lot for older children to do. I know I will be leaving Madison before my child enters high school. There isn't enough here for my child to thrive. Madison is very small with very limited activities. In addition, there's no good mass transportation system here. No train, no large airport, so for reasonable ticket prices we have to travel to Milwaukee or Chicago airports. For my husband and I, activities for us are very limited. If we want a nice theatre experience or other real options, we have to drive to Chicago, or at the very least Milwaukee. We definitely have a two year plan to vacate Madison, my child is going into seventh grade now, we will be gone no later than his middle school completion.