Hi Jenny,
Good questions! My little guy didn't want the helmet on either (he's 3) but learned really quickly that no helmet means no ride! They do associate it with going for a ride and will look forward to it. They will adjust to having it on their heads but I find he gets really antsy after an hour in it. Make sure to take along snacks, sippy cups or even some small toys you can attach to the trailer. Plan for areas where you can stop and they can get out and stretch their legs and burn some energy.
I use a hybrid bike with the trailer because that's the one I have my kickstand on. I looked for a lighter trailer and bought a used kids caboose that weighs in at 20 pounds. It has a rain flap and I would have prefered one that had the shaded windows. Ebay has a TON of auctions on trailers so you may want to check them out. Burley is the top of the line, and I've found the Schwin and In Step ones to be the lower end and heavy - 30 pound range.
He fought me tooth and nail the first time we rode. You would have thought I was killing the kid! I rode on the sidewalk a couple of houses down and back and he calmed down. I needed to get an animal figurine that he could "take for a ride" and we were off! He's my little cheerleader - faster mom, you can do it, etc. It's pretty funny.
I think most of them have the roll bars, just make sure they do. A roll bar will NOT protect them without a helmet. I don't see how he can make a good arguement on not wearing a helmet. One "small" accident that slams a baby's head into the pavement and no more baby. Definitely not worth it to any parent. Tell him to tone the screaming outHave fun and enjoy the freedom. I have found pulling the trailer to be a great leg workout on the hills.



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Have fun and enjoy the freedom. I have found pulling the trailer to be a great leg workout on the hills.
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