runDisney feels like it has been around forever. It hasn't. The name itself only dates to 2010, and the first Walt Disney World Marathon was in January 1994, with about 5,600 runners.

In this episode I follow the thread of each of today's four race weekends back to where it started: Marathon Weekend, from that first marathon to the half, Goofy and Dopey; Wine & Dine, from the Disney Classic 10K and the Tower of Terror 13K to the night half marathon; Princess, from Mini Marathon Weekend to the race that changed who runs runDisney; and Springtime Surprise, by way of Disneyland, Tinker Bell, Star Wars and the Rival Run. This is Chapter Two of The runDisney Companion.

LINKS
This episode's article and the runDisney history timeline printable: https://thecastlerun.com/history
All the printables: https://thecastlerun.com/printables
Running Wine & Dine this month? My 2026 guide: https://thecastlerun.com/wine-dine-2026-guide/
The new 5K start groups at Wine & Dine 2026, explained: https://thecastlerun.com/wine-dine-2026-5k-changes/
run. eet. repeat. Book signing at eet, Thursday, October 22, 3–6 p.m., benefiting Kellsie's Hope: https://thecastlerun.com/eetWD
MEI-Travel & Mouse Fan Travel: https://thecastlerun.com/MEI

NEXT WEEK
Registration: how it works, how to maximize your chances, proof of time and Club runDisney.

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.

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.

Before we talk race weekends, corrals and costumes, I owe you the story of how I got here. I wasn't a runner. I wasn't a Disney person. I was a Big Law attorney working 100-hour weeks when my dad got sick — and one day my body refused to sit still with what I was feeling, so I put on my sneakers and ran.

A heads-up before you press play: this episode talks about a parent's illness and an end-of-life decision. If today isn't the day for that, Episode 2 is out now too, and you can always come back.

This is Chapter One of The runDisney Companion, told the way I'd tell it across the table: the first run, the first Disney trip after we lost my dad, the 2016 Princess Half Marathon, the post-race crash nobody warned me about, the phone call that got me out of law, and the move to a home a stone's throw from Cinderella Castle. One hundred runDisney races later, here we are.

BOOK PARTNERS
They're companies my family and I have used and trust.
MEI-Travel & Mouse Fan Travel: thecastlerun.com/go/MEI

FIND ME
https://thecastlerun.com
Instagram: @thecastlerunner

CHAPTERS
0:00 Cold open
0:15 Welcome to The Castle Run
2:25 Chapter One: how I came to be the person writing this book
3:28 Big Law and the house of cards
4:18 My dad's diagnosis
5:54 The first run
6:59 My 36th birthday
8:09 Why I kept running, and our first Disney trip
11:38 Finding runDisney: the 2016 Princess Half Marathon
12:35 The post-race blues
13:15 "Put a date on the calendar"
14:07 Leaving the law and moving to Windermere
15:14 100 races and The runDisney Companion
16:05 A quick note, and my book partners
17:49 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.