There seems to be a lot of variation on this between schools. At ours kids can go out within town (5 mile radius maybe) without asking for permission assuming they are going to be back in the dorms by the required time. There are some walkable places but most of the stuff they want (movies, big box stores, Starbucks, places to eat) are a couple miles away so they Uber. You only have to ask for permission if you are planning to leave town. School provides shuttles to airports and cities before the breaks and also for outings planned by the school/clubs but not for run of the mill Target trip.