Hi Jessica,
Welcome to planDisney, and thanks for your question about the how to capture all the stunning decorations for fall and the holidays in one Walt Disney World visit.
I can never decide which season is my favorite at Magic Kingdom, the rich orange highlights of the fall decor or the festive sparkle of the Christmas holidays. So rather than choose, I always try to see both.
The fall decorations are in place by the first
Mickey's Not-So-Scary Halloween Party, which typically takes place in mid- to late August. By then, Main Street USA is festooned with pumpkins and fall leaves, flowers and bunting. Those decorations remain in place through the final Not-So-Scary party, which usually takes place on October 31 or November 1.
Then, truly like magic, fall melts into Christmas virtually overnight. Within a couple of days, the holiday decorations are fully in place at Magic Kingdom, in time for the first
Mickey's Very Merry Christmas Party, which normally occurs a week into November.
The Christmas decorations roll out more gradually across the other theme parks and resorts, but most are installed by mid-November.
I'm not sure how long your vacation will be, Jessica, but if you arrive on October 28 as planned and stay for several days, you certainly should be able to enjoy some early Christmas cheer and maybe even the first Mickey's Very Merry Christmas Party.
You also will be able to enjoy one of my favorite "holidays," the
Epcot International Food & Wine Festival, which typically continues until mid-November.
Please let us know if you have any other questions. We're always happy to help.
Enjoy every magical moment,
Wilma