My daughter, recently 4, enjoys long outings of sidewalk-biking now. We’ve gone and 3 and 4 mile trips so far. At each crossing, we asses the traffic (or lack of) together and I give her the signal to cross. Here she’s crossing from one sidewalk to another on an empty neighborhood street. She has a light up front to help see sidewalk and road hazards as it’s getting dark. Sometimes she also wears a reflective belt for evening outings, although she doesn’t have it on here.