I start having the children practicing to walk beside the stroller at about 18-20 months while attached to my wrist. But that's just an average. Today at the park my 17 month old dcgirl was walking around holding onto my stroller and since she was walking before she was a year old and is actually bigger than my 23 month old dcb, why not start her at practicing? It takes a few months of practice before they can go in a straight line for a whole block. But all the children are different, some are very clever. I would start your little guy for sure!