How old was your LO the first time he or she went trick or treating- like actually went up to doors and held out a bag?
C was only a few months and at her very very fussiest for her first Halloween, so I put her in a hand me down Halloween onesie and called it a day. Last year we went to the Halloween event on our Main Street and walked around, but she was still too small to get it at all and I didn't want to walk up to stores with the stroller and ask for candy (for me!).
Now she is a little over 2 and walking and talking so I think she might have fun but it might also be overwhelming. I don't think we'd go door to door but probably just do the afternoon even on Main Street again. Then steal any candy she gets anyway.
We also go to pre Halloween parties and stuff so she can wear her costume.