Yesterday I did a few loops where I go down NH to 198, then downhlll to Firestone. Then up Firestone, through Hampshire Greens to Ednor. Then over to Alexander Manor and through that development to Rt. 108 in Ashton, then back down NH to do it one more time.
I call that my Boring Loop - 20 miles or so I can sneak in at lunch or early in the day but I've done it a jillion times over the years!
When my daughter was little, I had a Winchester trailer but Hampshire Greens didn't exist! When she was older, I got one of those third wheel bikes and we'd bike to Cloverly Elementary school in the morning. We had a lot of fun with that trailer on vacation and on some of the local rail trails.
Back then, I wrote a book "
Family Bicycling in the Baltimore Washington Area" - many of the routes haven't changed that much but many more choices now.