I wish I had advice but I can only offer sympathy. My three year old son is the same way. He is timid about everything new and different and sometimes even things that he has done tons of times before. I even try to prepare him before the events by explaining in detail what is going to happen but it doesn't help. He also does handle any change well. Even going from season to season and having to go from shorts to pants, shoes to sandals-he has a total meltdown. Very frustrating....

My just-turned-6 yo son had many of the same issues - he was extremely fearful of people in costumes (so we did not "celebrate" halloween or even go anywhere where there was a mascot, or to parades), he also had what seemed to me to be an excessive fear of dogs (small and large - nothing ever happened to him with a dog) and large farm animals - in all these situations he would visibly be shaking and just terribly terribly frightened - it wasn't just when he was with me - it happend on school trips, everywhere! But Just a couple of weeks ago, something magically changed - he let go of his fear of dogs - and spent a full weekend petting and playing with a large dog (luckily a friendly one!) and now says he is not scared of the other things any more either (though I still notice a little nervousness). My advice is to honor their feelings, don't put them in situations so that they will 'get over it', and just manage your life as best you can avoiding the things that scare them. I think they will grow out of it on their own and will also learn that they can be different than others but still ok. I know that won't help very much with scared of the dark and going to sleep, but I also leave my son's bedroom light on when he goes to sleep - it doesn't keep him awake, and it seems to solve his fear of the dark. Hope this helps