I once tried to get my 21 month old daughter to walk to the bus stop, and it didn't end up going so well...but I'm the kind of person who gets VERY stressed out about safety, and I feel much more comfortable having them strapped into a stroller, until they get a little bit older. I had tried with one of those backpack harnesses. The thing with toddlers is once you actually get to the bus stop, most of them are not content simply waiting. They want to play on the snow bank, do things they shouldnt and next thing you know you are pulling your hair out! I'm sure others have different experiences to share but this was mine.