Solution: Let's take these one at a time.
Where: The obvious choice is your neighborhood and there is nothing wrong with that, provided your area is safe enough and the houses / apartments are close together. At this age, you'll be going with the kids, so you'll provide for them should anything confusing arise. Where I grew up, the houses were very far apart, so my parents would drive us to another neighborhood and follow us as we walked the streets, either by walking or by car. If you don't care to try your luck with random people in a random neighborhood, many public places hold safe, inside, trick or treating. Try your local grocery store, mall, churches and amusement parks for organized trick-or-treating events.
Costume: This is usually the child's choice, but take into consideration where you live. Are you in New England? Because it's snowing up there. To avoid conflict right off the bat, start suggesting costumes that are by nature warm (like a gorilla or a wolf) or a costume that a coat can easily fit underneath (like a snowman or Big Bird). Even better, suggest costumes where coats are part of the package, like a firefighter or a skier. Here in Florida, we don't have to worry about that.
How long to stay out: Again, pick up cues from your kid. If they show any signs of tiredness or irritability, start heading them home. They'll most likely want to stay out all night, but that's not a possibility, so really any time you cut it short will be treated like a travesty, whether it's 8 p.m. or 11 p.m. My family won't want to stay out until too far after dark, since we'll be trick or treating in the neighborhood and not in some organized event.
Make sure you match your child's candy bag to her age, too. I'm a glutton for candy, so you bet I want to arm my kids with queen-sized pillow cases, but I refrain. They'll be carrying little purses as part of their costumes, and the candy will go in that. The candy is for them, after all and they don't need pounds of it. Plus, it's easier for them to carry, even than those cute plastic pumpkins.
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