My best memory of Halloween was when I dressed up as a Broccoli and was on the Mid Morning Show on Fox 5 in NYC with Bill Bogs.

While I don't have a video of it...I do have a clip from one of his shows:

And now I am thinking I need to find this video of me....the hunt begins.
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My best memory as a kid was when I was 15 sadly. I dressed up in a Geisha style costume. My boyfriend at the time being as short as he was tried to be a midget for Halloween. He tied roller skates to his knees and tried to skate around like that. The little kids were all laughing at him. It was so funny to water. It had to be the best Halloween I had ever had.
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When I was younger, every Halloween was all about dressing up and singing Halloween-ish songs and telling goofy jokes.

My mom would often dress up along with my sister and I when we were little. She was usually a witch. We would go to relatives' houses and she would make us sing Halloween songs like "Three Little Pumpkins". If we didn't sing along, she would sing anyways. I was always embarassed!

Then, we would go trick or treating with our cousins. The majority of the houses we went to wanted the kids to say funny Halloween jokes in order to get candy. I always worked hard to remember the best jokes like "What do you call a witch who lives at the beach? A sand-witch" so that I could get candy. As a 5 year old, I thought I was the coolest person in the world with my clever jokes and well deserving of the candy.

Looking back, the singing was actually really fun and my jokes were rather silly (and they would have given us candy regardless if we had a joke or not). As a child, it was a great time though and the singing and jokes are some of my fondest memories of Halloween.
Source(s):
http://stepbystepcc.com/pumpkins.html

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Chicago does things different from the typical Halloween. When this most terrifying day approaches Chicago turns into a battle field with paint gun riffles and egg grenades. When I child I was caught in the cross fire in my superman costume my mother bought from the local Walgreens down the street. My friends and I was carelessly walking door-to-door collecting treats from known neighbors. A couple of teens were on their bikes looking for innocent bystanders to egg on-site, with their book bags filled with cartridges of paintball pellets that swells the skin as soon as it makes contact.

The sun was slowly declining and night was soon to follow. By this time all of us were on our way home thinking of all the treats that we gathered for the night. We seen the teens pull up slowly but there was nothing we could do to avoid the humiliation that we were about to face. My friends and I stood there in a group while yolk and paint covered our bodies. My superman costume no longer had the appeal of the blue, yellow, and red colors. So while I was walking home crying my eyes out I was thinking that the day could not get any worst. My mother comforted me with a wipe of a towel and a hug. The best thing about the day was that I did not lose my candy.
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I was an astronaut one year when I was in elementary school, I had a silver and gold suit built out of costumes my mom found at the local theater (she worked there) - And we used one of those office water cooler jugs as my helmet. I won best costume at my school and was interviewed on the local news who was covering the all important event.

All is good right?

No so fast, when it came to trick-or-treating it was a pretty cold and rainy Ontario evening, my jug fogged up and became inoperable, and I had to wear a winter jacket over my suit... So basically going door to door I looked like a regular kid, having to explain over and over that I really did have a great costume.

At the end of the day, all I really wanted was candy.

Seinfeld illustrates it well here.
http://www.youtube.com/watch?v=Lfk2me7p9us
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I was probably 7 years old and dressed like a Cowboy I think. I remember it best because it was the only time my dad went with us when I went trick or treating. He was a truck driver and out of town often. It just happened that one year he went with us.
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Sad truth is that trick or treat isn't known here in our country during my childhood days. It was adapted here when I was already in high school, which is, obviously not for me anymore since I'm tool old by then.

Maybe my fondest memory is that everytime me and my brother would watch scary movies and series on TV. Then when I see him getting scared already, I will throw something on his way making him shout. lol he's always been the coward one between the two of us. ^^ He wouldn't even turn down the lights when we're about to sleep (we share the same bedroom before). That brother-sister bonding matters a lot to me that's why that's the best memory I could think of.

Hmm, if ever there was trick or treat here years back when I'm still a kid, I'll probably be a beautiful white lady. White lady is so common in our country. Most people here claim that they already see one. So I think that's the first idea that will pop in my head during those years. :)
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Oddly enough, my best memory of Hallowe'en is of my father, not me. I came home when I was probably 12 and mom was putting makeup on Dad. Mind you, Dad was probably about 60 and, although he loved a good laugh, wasn't one to dress up. So seeing mom making his face pale and putting darkening the circles under his eyes was a shocker. When I asked what was going on, he said he was going trick or treating. That was a first, and since all the kids in the neighborhood had pretty much grown out of the practice, I couldn't imagine that he was going to get much in the way of candy.
Draped with a white sheet, Dad looked pretty good as a ghost. Then he picked up a martini glass and out he went. I honestly can't remember if Mom went or not. I expect she tagged along, a little embarrassed and about as shocked as me.
Dad went to several homes in our neighborhood, knocking on the door and offering his glass saying, "Trick or Treat!" when they opened it. Everyone had a good laugh, and almost everyone filled the glass. He ended the night at the nearest neighbor's (very rural - probably 1/10 of a mile away) and got seriously cheerful, then walked home in his sheet.
I don't know what came over him, but it's one of my fondest memories of him.

http://farm1.static.flickr.com/110/283576582_ba533bf195.jpg
Source(s):
Memory

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One year when my sister and I were trick-or-treating with our two cousins, we happened on a house that gave out full-size Hershey bars! We were all stunned!

When we had walked back down their really long driveway to the street, we had a little meeting. My older cousin organized us to all exchange peices of our costumes so that they wouldn't recognize us, and then we went back up to the same house again!

LOL! It was so fun!
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I was 15 and in the 10th grade.

I bought a bottle of liquid latex and a bottle of spirit gum from a theatrical makeup place with all the money I had.

Then I went around to the barbers and volunteered to sweep up their clippings for awhile, until I had enough hair clippings.

I put some sand in a box and pressed my face into it to make a mold, and then poured melted paraffin wax into that to make a 3D busk of my face.

I used that as the base to apply the liquid latex, to make a latex mask.

I glued the mask and the hair from the barbers to my face with the spirit gum, and used my mom's makeup to give it flesh tone and depth to the eyes...

And went to the high school Halloween party as Cornelius from Planet of the Apes.

I got into the high school year book.

I looked like this:
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Mine was when I was about 6 yrs old. I dressed as Wonder Woman.That was HUGE back then.
I was so excited to get home from school to go trick or treating. Shortly before school let out it started to SNOW. Once we got home and got ready to go out,We had already 3 inches of snow on the ground.We had to wear boots, hats and gloves.No one could see my AWESOME costume.I was wrecked for a whole year over that one.LOL!!
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One Halloween years ago I was out trick or treating with my mother and a man with a carved pumpkin 'instead' of a head sneaked up from around the bushes and scared the hell out of us.

We ran for a bit, continued walked, then he did it again a good twenty minutes later from another station before taking off the pumpkin.

I'm still not sure if my mother or I were more freaked out, and I can't imagine the effort and discomfort of that 'costume' but it was one of the best I've ever run across. Very Sleepy Hollow.
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