Four runDisney race weekends, one season, and one question: which one is yours? Here's how to choose — and why you shouldn't overthink it.

In this episode I walk through Wine & Dine, Walt Disney World Marathon Weekend, Princess, and Springtime Surprise: when each one falls, the longest race, the challenge, the theme, which courses run through Magic Kingdom, and who each weekend is for. This is Chapter Three of The runDisney Companion.

2026–27 SEASON
Wine & Dine Half Marathon Weekend: October 22–25, 2026
Walt Disney World Marathon Weekend: January 6–10, 2027
Princess Half Marathon Weekend: February 25 – March 1, 2027
Springtime Surprise Weekend: April 8–11, 2027

LINKS
The new 5K start groups at Wine & Dine 2026, explained: https://thecastlerun.com/wine-dine-2026-5k-changes/
MEI-Travel & Mouse Fan Travel: https://thecastlerun.com/go/MEI

NEXT WEEK
The history of runDisney, and how each of these race weekends came to be.

CHAPTERS

0:00 Cold open
0:11 Welcome to episode two
1:12 Don't overthink it: what every race weekend shares
2:36 What's different: timing, distance, challenge, theme, course
4:30 Wine & Dine Half Marathon Weekend
5:39 Age requirements by distance
6:11 My first Wine & Dine, and its night-race roots
8:50 Walt Disney World Marathon Weekend
12:49 Why Dopey makes this my favorite weekend
14:15 Princess Half Marathon Weekend
16:12 My first race
18:38 Springtime Surprise Weekend
22:01 Virtual races
22:48 So which one? Don't overthink it
23:36 The book, updates, and MEI-Travel
24:10 What's next

THE BOOK: The runDisney Companion — https://thecastlerun.com/book
UPDATES: the Companion Hub — https://thecastlerun.com/companion/
New episodes Tuesdays at 5 a.m.

Book partners are sponsors of the book. There's no affiliate relationship; I don't earn anything when you book with them.

The Castle Run podcast and The runDisney Companion are not endorsed by, affiliated with, or sponsored by Disney or runDisney.