I was on the Disney Magic last Halloween and some of the Disers put together a similar trick or treat event for the kids. It was a lot of work for them though. I guess it would come down to having someone willing to organize the event (and figuring out how to buy & transport the candy - or if each participating cabin would bring their own type of candy).
I don't think we are dressing up on the ship this year. Last year the costume finalists were up on the step in from of Lumiere's in the atrium (on the Magic). Because my mom is in a wheelchair there was no way she could have been a finalist (because of the step and lack of ramp). My rule is if I'm with my mom, and she can't participate in something she'd like to (because of the wheelchair), then I don't either.
Last year we had planned to go to the parks for 1 or two days before the cruise but then I changed my mind since I was concerned about the heat and getting a sunburn and just generally being too tired to enjoy the first day or so of the cruise. We're driving down and staying at the Holiday Inn Express in Cocoa Beach (at least that's what I have booked right now!). We'll just have dinner somewhere in the area and get a good night's sleep before boarding the ship.
I'm still undecided about whether we should show up at the port super early (like 10:30am) or late (like 1:00pm)? Anyone else thinking about that yet?
I plan on bringing a costume even tho I am sure I will not be entering a contest, because it will just be fun to wonder the ship in costume, really feels in the Disney mood then (just like pirate night when in gear). So, yes, I will have to bring two costumes, one pirate and one Halloween.
Hadn't thought about bringing candy for a DIS'er ToT, but I could be persuaded to bring a big bag with us on the plane (assuming, TSA doesn't claim it first

We will be spending the pre-cruise night an AKL (like we do every cruise), it may not be the park but, the next best thing..