Episode Timeline · 5:05pm Oct 15th, 2014
Before I post today's story update, I am going to do this blog post detailing the correlation of "Canterlot Chronicles" episodes to the canon show episodes. The summaries won't always make it clear when a certain story happens, so when I start a new story this post will be updated accordingly.
Part of the problem of writing fanfiction "interquels" in Friendship is Magic is that you're limited by the fact that the show itself is very vague on the passage of time. In Season 1, the best that can be said is that because of the "one letter a week" requirement, the season has to last at least 24 weeks in-universe (24 episodes after pilot -> 24 letters -> 24 weeks), starting with the pilot probably occurring at the summer solstice (longest day of the year - most symbolic for "the triumph of the sun") and ending somewhere near the end of that year.
But here's the catch: some episodes are clearly out of chronological order ("Fall Weather Friends" shown AFTER "Winter Wrap-Up", for one thing) and "Winter Wrap-Up" seems to imply a longer time span for Season 1 than 24 weeks (something closer to 9 months, or the following year's spring). Until and unless the show writers come up with a more concrete chronology, I am having to write around those limitations and certainly think there is room for disagreement in any conjectural timeline. If anyone wishes to comment with their own critiques or suggestions as how to improve this timeline, don't be afraid to do so.
All that said, here's my "Canterlot Chronicles" timeline relative to the canon episodes. "Season 1" will last through the canon show's Season 1 and the gap between the first two seasons and end before the canon Season 2 premiere.
The Canterlot Chronicles: Season 1
"It's All Real" + "The Long Road Home" -> During "Friendship is Magic, Part 2" (aka "Elements of Harmony")
"One Good Stallion" + "A New Mission" + "The Luna Shift" -> Between "Friendship is Magic, Part 2" and "The Ticket Master"
"Cadance" -> Between "The Ticket Master" and "Applebuck Season"
"Games We Play" -> During "Applebuck Season"
"Excelsior" -> Around "Griffon the Brush Off"
"Buck Nothing" -> Between "Griffon the Brush Off" and "Boast Busters"
"Operation Shield" -> Immediately after "Boast Busters"
"Broken Fences" -> Between "Boast Busters" and "Dragonshy"
"Pocketful of Posies" -> After "Dragonshy"
"In Praise of Twilight" -> Around "Look Before You Sleep"
"Zecora" -> After "Bridle Gossip"
"The Parasprite Project" -> After "Swarm of the Century"
"High Fashion, High Noon" -> After "Suited for Success"
"Circle of the Moon" -> Around Nightmare Night mid-Season 1, before "Fall Weather Friends"
"A Hearth's Warming Caper" -> Winter before Hearth's Warming mid-Season 1, after "Fall Weather Friends" but before "Winter Wrap-Up"
"Rainboom Revolution" + "Consequences" -> Immediately after "Sonic Rainboom"
"The Crusaders" -> After "The Show Stoppers"
"Mission to Appleloosa" -> Around "Over a Barrel"
"Phoenix Down" -> After "A Bird in the Hoof"
"A Just Cause" -> After "Best Night Ever" but before Season 2
The Canterlot Chronicles: Season 2
"The Day of Discord" -> Around "The Return of Harmony"