Halloween is often called a crossdresser's favorite holiday but that isn't the case for me.
First, I want to say that I do like Halloween, it's just not my favorite holiday. I have a serious sweet tooth so I always enjoyed trick or treating and getting a lot of candy! My favorite Halloween candy is Brach's mellowcreme pumpkins which, for those who don't know, are basically pumpkin-shaped candy corn. I also enjoy Hershey's almost annual special Kisses; I like this year's Candy Corn Kisses but I loved last year's Pumpkin Spice Kisses and hope they'll bring them back sometime. I also do enjoy dressing up in a costume but because I have the opportunity every few months to cosplay at an anime convention, Halloween isn't the only day out of the year that I get to wear a costume.
One of the main things I don't like about Halloween is getting scared. I don't like horror movies and could do without the 5 million commercials we get for them on TV at this time of year. I also don't like haunted houses or anything else that involves being scared so one of the main attractions for many people on Halloween isn't something I'm interested in.
After my sister and I outgrew trick or treating, it became my family's tradition on Halloween to turn off all the lights in the house, get the bowl of my Mom's chocolate spiders and sit down to enjoy a non-scary Halloween movie. Occasionally we'd watch something like Frankenstein or Bride of Frankenstein but the main movie we'd watch each year was Abbot and Costello Meet Frankenstein. I still have fond memories of that film and will be on the lookout for it on the movie channels each Halloween. I've continued the tradition on my own by watching a movie around Halloween, usually Young Frankenstein or The Nightmare Before Christmas.
Even without enjoying being scared, most crossdressers still say Halloween is their favorite holiday because it's the one time each year that they can go out in public en femme. As a kid, I had a strong desire to dress up as a girl in some way every year but I was never allowed to because my parents were so against it. I only started dressing en femme at Halloween in college after I had already become more open about being transgender. So Halloween always led to a feeling of disappointment instead of being the one occasion where I could be free to be who I am.
Also, as I take my first steps toward becoming a woman, I am dressing full-time so being able to dress en femme in public is not a unique thing that I can only do at Halloween.
I do still enjoy Halloween and am looking forward to the party I will be attending this year but, unlike many other crossdressers and transgender people, Halloween isn't my favorite holiday.