Mine are now 14, 11, and 10 - we never used a stroller past 4 years old. Anywhere. Stroller free is easier and when the kids got tires we went to the pool. It was never an issue. As a teacher - not judging, but an observation - I find it strange to see an older child in a stroller. It isn't a big deal when I see a younger child not using it and an older kid sitting in it, but it is developmentally worrysome for an older child (6+) to need a stroller without underlying issues.