You’re going to Waldorf, right? What route do you take?
I might start taking my daughter to Arsenal School by trail-a-bike at some point, which seems to be a subset of your route. I scouted a route part way there through Frick Park, from Commercial Drive to Reynolds St. I’d definitely consider doing that with the trailer for that part of the ride. But I’m interested in what alternatives you might suggest, especially for the other end.