Hello Eralynn!
Welcome to the Disney Parks Moms Panel!
What a spook-tacular question! I'm happy to tell you, our favorite "Pumpkin King" does like to make some very special appearances at the
Walt Disney World Resort. Every year, there are two events I look most forward to at The Most Magical Place on Earth:
Mickey's Not-So-Scary Halloween Party and
Mickey's Very Merry Christmas Party. I like to visit Jack Skellington from The Nightmare Before Christmas during both; Jack dresses up as Sandy Claws during Mickey's Very Merry Christmas Party and it may be my favorite thing about the entire event!
The good news is that these events are celebrated on select nights for several months. Although details for the events in 2020 have not yet been released, Mickey's Not-So-Scary Halloween Party last year started on select nights in August until November 1st. Mickey's Very Merry Christmas Party ran through select dates in November and December. Event dates and Character appearances are subject to change from year to year, so be on the look out for further details to be released about the parties.
Jack Skellington greets Guests only during the parties and the
special ticket events are quite popular. Be sure to plan accordingly so you're able to enjoy it all. When I attended Mickey's Not-So-Scary Halloween Party, I've noticed Guests are usually allowed entry into Magic Kingdom Theme Park at 4 p.m., and I've been able to meet Jack Skellington and Sally at Town Square Theatre beginning at 4:30 p.m. I would get to the entrance by 4 p.m. so you can head on over to the theatre and grab your spot in line. That way, you can enjoy Boo-to-You Parade, which is my most favorite parade in the world!
I hope you have the most magical time, Eralynn!
Aena