Centerfield

I used to have to drive my daughter around for about half an hour to get her sleepy or asleep.

The real smart thing to do is have a strictly established routine so that everything is quiet BEFORE you start getting the kid ready for bed.
I would always read to my kid and this would be after she brushed her teeth, got her bed ready and had gone to the bathroom.

I still have the library.
Stella Luna, Fox in Socks, etc.....

I've found that a glass of warm milk and Cspan normally does the trick.

Been there. Done that. The driving around thing works for some kids. A late bottle & cuddle in recliner in front of boring low-sound TV. Don't let the afternoon nap go on too long...as nice as that break may be.

But it's all a crap shoot.

Thanks for all the advice.

The Kid sometimes likes C-SPAN (really)! Usually when there are grandparently people or women. Austin zoning hearings are pretty reliable sleepers for him, though. Probably I should record one and play it back to him every evening between his bath and bedtime.....

Our kid is one of the few who DOESN'T go to sleep in a car. At three months, we had to turn down an invitation in the next city to the south because he was crying every time he was in a car. He's over that, but he still doesn't reliably sleep. At least we can make long car trips now, though, because he does get really into the scenery when not asleep.

Not too late on the bottle, milk isn't good to keep on a kid's teeth late into the night. Might try a little water at the end.

Even toddlers can get cavities.

As far as crying, live with it. Ibet your kid couldn't beat my kid who could go for up to 3 hours on a single charge.
I got to the point where I'd let her cry it out, give her some water to drink to calm her down and go on.