That’s a tough situation: Your toddler wants independence; you don’t want to be chasing him around all afternoon (and you really don’t want to lose him!).
First, try and figure out why your toddler hates the stroller, and then you can figure out a solution. For example, are you using one designed for babies that doesn’t let him sit fully upright? Then maybe it’s time to upgrade to a stroller designed for older children. You might want to try a completely different style. Some toddlers love stand-up strollers. And some toddlers who resist strollers are more than happy to ride around in a wagon.
If your toddler seems bored in the stroller, try attaching some new (or haven’t-seen-in-a-while) toys to the stroller using plastic links or a stroller-toy attachment. If he resists the stroller because he’s forced to spend long hours in there while you run errands, try taking him out of the stroller every so often to walk around. (Yes, it takes time out of your day, but if your toddler isn’t screaming, it just may make finishing your errands less stressful).
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