First off, I'm not a big fan of solving problems I don't have. Currently, your routine works: you get exercise, you DD enjoys the stroller and she's otherwise getting plenty of fresh air and exercise. 5 year olds are a lot different than 4 year olds. Next winter you will be doing things differently, and the solution you find will be dependent upon your needs and her needs.
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Originally Posted by Yooper 
I agree that children walking is healthy for them in many ways.
The bus is not an option as we do not have one.
And the more I think about it, this is more about the exercise walks rather than errands. Technically, I could do all of the errands in the evenings and weekends when I can use dh's car. I just happen to walk right past many of these places while on my fitness walk that it is easy to kill two birds with one stone. And it opens up the weekends and evenings for family fun rather than errands. Not to mention better for the environment. But really this is about the fitness. I seem to physically and spiritually need daily outdoor fitness time and I do not see that need going away anytime soon. I just cannot seem to figure out how to continue my walking for fitness habit once dd is too big/old for the stroller yet not fast enough or agreeable to walking those distances herself.
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So what are you teaching her here? You are teaching her that (1) you don't need a car to do your errands, (2) you can fit exercise into your daily routine, (3) you can address your physical and spiritual needs by spending a lot of time outside, and (4) you don't have to hide inside just because it's winter.
I think those things outweigh any imagined problems of what your routine will look like once she outgrows the stroller -- physically or emotionally.
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Originally Posted by Yooper 
Biking is a problem in our city. We have very steep streets, no sidewalks, and a lot of drivers that are not aware enough for me to be OK with dd on a bike for quite some time. She does have a tag-a-long bike and we do take bike rides almost daily in the warm months in addition to our walks but we have to go on a special loop that does not go anywhere near the places I go for errands. That is a good solution to the exercise question though. We could go on longer rides to give me the fitness component. But winter is still a problem. And winter is VERY long here.
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I am quite sure she is capable of walking the distances I do. I just do not believe she will be capable of doing it at a decent pace for a few years yet. Nor do I think she would be agreeable to walking those distances day in and out.
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On the bike, I did two things: I started taking DD out daily on her bike. We'd go to the park or the pool (<half a mile). I started off by jogging with her to help her learn the rules of the road -- staying to the right, looking for cars, stopping at intersections, etc. I also sent her to Safety Town, a program for kids entering kindergarten in our town. It was a great program that had kids out on a mocked-up road to teach them the rules of the road. By the end of last summer (DD turned 5 in August), she was capable of controlling her bike, communicate appropriately with drivers, etc. I would walk, jog, or ride with her confidently now.
When you do have her start walking with you, maybe you can transition over a period of time. Have her hop out of the stroller for the last half mile of your trip, gradually increasing the distance. We'll play games or racing to the corner, skipping or hoping along, see who can walk backwards faster, etc. DD now just walks with me, generally at my pace.