I've been running over 1000 miles a year with my jogging stroller for the last decade and more recently added in biking with a trailer and trailer bike. I've collected some fun ideas to bribe- I mean encourage - kids, as well as mechanical advice for maintaining your equipment.
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How do you like your BOB? My wife and I have had ours for 5 years and started a site dedicated to our little infatuation. :)
We've taken it in areas that look just like where you're going and it's held up very well.
Keep on strolling!
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