I have a really mixed experience of Hallowe'en.
I grew up in Scotland, where Hallowe'en was noted with apple bobbing and readings of Tam O'Shanter. There was a mix of traditions between Hallowe'en and Guy Fawkes in the custom of Guising - Penny for the Guy, but dressed up in ghoulish costumes. We were never allowed (or wanted to) do this ("not quite our class dear"), but we always made guisers work for their money.
Living in England, it's a case of 'trick or trick'. Revellers are seriously disappointed when you offer them a fun size Milky Way, when what they really want is to egg your house.
In the US, it is a totally differnt thing. It is not particularly focussed on the dark - costumes can be anything, so it is easy to dress up young children. Communities really rally around and make it as much fun as possible, and even British expats can shock the neighbourhood by serving mulled wine to all adult chaperones (shocking to Brits by serving it out of season, but shocking to Americans because of the alcohol content).
To me, T or T is an American tradition that we have only adopted in a piecemeal way. If it is to work here, it has to be adopted hook, line and sinker. That means that everyone in a community has to get behind it and play along with it. It can be fun and community building.
The big issue I have with Hallowe'en is that it is revelling in the dark. For our family, this is pretty easy to overcome by giving treats rather than demanding them. Howver this is a sticking plaster over a bigger problem.