Living in a rural area as we do, trick or treating from home is not an option (lot sizes start at three acres and go up, and there are no sidewalks) so of necessity, people around here bring their children to one of the two or three nearer towns on Halloween evening. One town in particular is legendarily amazing--and mobbed--on Halloween...entire streets are closed off for trick or treaters and the owners in that area take great pride in the spookiness of the decorations that fill the porches, facades and yards of their large Victorians. We've been bringing the kids there since Petunia was four or so.
Petunia is far from the timid, shrinking wallflower sort, but at eight, she is still a small person. We encourage our kids to just bypass any house they think is too frightening, and last year Petunia took one look at a particular house and actually crossed the street to avoid it! To be fair to her, it was creepy as hell, even to me...a hearse in the driveway, hooded Druids roaming the front yard amidst great billowing dry ice clouds, and a shrouded 'body' dangling from an upper balcony. Can't say that I blamed her one bit, but apparently this attack of nerves has been bothering her for the past year.
Some friends of ours in that town host a Halloween party every year, and as soon as it gets dark everyone walks over to the closed-off area to trick or treat. We'd no sooner left the friend's house than my little princess (gown, tiara and all--very regal) looked up at me very solemnly and said, "Mom, I'm going to that house this year." I told her that it was entirely her choice and that she could decide when she got there. Along the way, she was unfazed by pirates, mummies, skeletons, giant jumping spiders and eyeball-dangling masks, so I figured she had a good shot at making it through whatever the creepy house was going to feature this year, but then we arrived and its only 'decoration' was a For Sale sign on the lawn.