So, my youngest is 14 years old in the 8th grade and he's as tall as me. I've been trying to discourage him from trick or treating this year. I think he's too old and it's getting ridiculous.
What do you think is the cut-off for trick-or-treating?
No cut off. But they need to;
1) get into the spirit, which includes properly dressing up.
2) make space/allowance for the littlies, and not turn it into 'Teenage-Lolly-Grab II : The Sugar High'.
My 12 and 14 year olds got fully dressed up and took their 2 year old sister trick or treating. They grabbed an early dinner, got dropped with friends, and then went trick or treating with peers.
In our local area, houses who want to be approached leave a pumpkin at their letter box, so I think that works just fine.