With the possible exception of Salem, Massachusetts, where the celebrations begin on October 1st sharp, I don't think any city celebrates Halloween as hugely as New York.
I remember being impressed, once upon a time, with the crowds of masquers I saw on Wisconsin and M in Georgetown, but that's nothing compared to lower Manhattan, where costumed crowds stagger about from SoHo to Midtown. Not to mention the fact that the city shuts down Sixth Avenue for an annual Halloween parade that always features, among other things, a reenactment of the "Thriller" video. (Like any big to-do in New York, you pretty much have to show up hours ahead of time to claim a worthwhile spot.)
It's kind of mysterious to see all the Halloween costume stores that spring up during October. Of course there are some year-round costume stores, and stores like Party City or Ricky's that are also around all year and bring out the costumes in October. But then there are the shops that suddenly appear in locations where they weren't previously, but whose previous occupant you can't quite recall.
Halloween was on a Saturday this year, of course. I made the mistake of thinking I'd be able to pick up a few props from a year-round costume store near work (New York Costume on Broadway) on my way home Thursday night. As the store came in sight, I saw one of those "lines around a Manhattan block" you always read about in the news when something new like Krispy Kreme comes to New York. Needless to say, I didn't bother.
On Halloween night, we ended up walking down St. Mark's Place and found that all the convenience stores and junk vendors were suddenly well stocked with wigs, hats, feather boas, etc. Gotta love the willingness of free enterprise to lend last-minute procrastinators a hand. (At outrageous prices, no doubt. I'm sure plastic cowboy hats that cost two cents to manufacture were going for $7.50).
Earlier that day, we ate lunch on the Upper East Side at a small empanada place. (Yes, Manhattan has multiple restaurants specializing just in empanadas. It's the Yuppie Paradise.) It was around a quarter to two in the afternoon, so I was surprised to see a little girl in a princess costume come into the place with her mother behind her. The mother asked the employees a question, and they smiled and nodded. The little princess marched up to the cash register, held out her basket, and received candy.
Trick or treating, Manhattan-style! She was not the only child we saw trick or treat in that restaurant. In fact, for the rest of the day, we saw lots of children making the rounds of local businesses. Somehow I never noticed this the previous three Halloweens. Seems surreal, doesn't it, compared to a suburban Halloween? But why should Manhattan kids miss out on the fun, just because they don't have cul-de-sacs and detached houses?