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I've seen it everywhere from Michigan to Florida. Some of the dogs are old. Some of the owners are old. If I thought our old golden wouldn't have freaked, I would have put him in a wagon. He loved being outside but couldn't walk very far, so he hung out in the driveway on a line most of the day, accepting treats from the neighbors. That didn't get me much exercise, though. Back when he was able, we used to walk three miles every evening when the sun went down. I think I was thinner then.
I try not to judge the little dogs in strollers, nor their owners. There could be reasons. There's a woman in our neighborhood who walks her little dog for a while, then puts him in the stroller, on and off. The dog likes to be outside, and she knows how much it can walk and when it needs a rest.

We have a high end pet stroller. Cat, no dog. Spouse uses a Rollator (walker) for Stability on longer walks, however they are bulky and take up a lot of room on walking paths.
Grab the cat, (empty stroller makes people think you lost a pet:1rotfl:) and pleasant walk for all. We only use stroller on walking paths.

In our previous neighborhood some used them to ferry box’s from the post and still get much need steps in.

I used to think that also. Then my dog got really old, but still wanted to be included. So...got a dog stroller so she could come along and she loved it. I was so embarrassed, but she was happy so.. ������

I’ve seen that a lot but never in the villages.

:-)