Updated October 22, 2020
I've always enjoyed Halloween back in Canada. As a child, I had a lot of really fun memories going out trick or treating with family friends, and later, my own school friends. I went trick or treating until I was way too old for it.
Trick or treating is not so common in Japan, though there are small communities that do more "controlled" type trick or treating.
In the first neighbourhood that I lived in here in Osaka, I saw a group of several families gather outside their homes with their children dressed up in costumes. It seems like they were getting ready to celebrate Halloween just within their small group. I imagine that they would just go around to each other's homes, doing some sort of a mock trick or treat.
I was actually surprised to see that happen, since I heard that trick or treating was non-existent in Japan. But I think it definitely goes to show that Japan has taken something and adapted it to suit their needs.
Going to a stranger's house and knocking on doors would not be something that's done here, especially with little children. There's no rule that people need to open their doors to give children candy, nor do people expect it. Thus if any trick or treating happens, it's definitely much more contained and only among people they know.
Theme parks in Japan are a big part of the entertainment culture, and they embrace Halloween and many of the big Western holidays quite well in their own way.
I thoroughly enjoy going to USJ for Halloween. It's nice to be around tons of people who just want to dress up and have fun, even if they don't really see Halloween as a festivity the same way we do in Canada. Not that we Canadians truly understand Halloween either.
But as long as people are having fun, right?
I think that's what counts the most. I don't think Halloween nowadays is really much of a serious type of festivity.
I'm not much of a party-person anyway, but if you do come to Tokyo or Osaka during the weekend of Halloween (or usually the weekend prior to Halloween if the day falls on a weekday), I do recommend checking out the streets for party-goers and people in costumes.
In Osaka particularly, most of the crowds and fun happen in Amerikamura (between Shinsaibashi and Namba). Some people may hang around Dotonbori or at least bar hop around there, so you will see tons of people in costume walking around regardless. It's quite an experience to see just people having fun and enjoying themselves with friends.
With COVID19 this year though, I would hope that the festivities would be halted... but see that people's attitudes towards the virus is becoming more lax, I absolutely think we will still see crowds out this year. Which is a shame since COVID19 numbers are still pretty much steady and not changed much daily since July and August. I want to have faith in people, but it's kind of hard these day.....
If you are thinking of going out, I do hope you would reconsider - at least not do any big group events for this year.
Be safe everyone!