I understand about having the little one out in the street. I haven't done that yet...not sure I will. Maybe when she's older and can handle the trail a bike concept.
The good thing about the Wildflower is it's relatively flat and it's out and back for the first 20 miles. You can go as long as you like and turn around at any point...not many rides work that way. I hadn't put in many miles prior to last year's ride and so a friend and I decided to just ride until we thought we needed to turn back...thought we'd shoot for 30ish. We felt so good after 20 that we commited to the 50, which turned out to be 54. There was one kind of ugly hill on the lake, but other than that just your averages rollers. Thankfully, the wind wasn't too bad either...hoping for the same on Saturday!