The 'verse: current story timeline (V2.0) · 8:50pm Jul 24th, 2014
This question comes up occasionally: if we put everything on a calendar, what's the order? It's been long enough since the last answer (with a few new additions) for a fresh one to be required. So I put the below on the Group, but I'm also posting it here for everyone else. This is not Group-exclusive material.
(Yes, there is Group-exclusive material. If you want to know what it is that badly, feel free to go look -- at your own risk. There be background stuff ahead... and since some of it is semi-spoilers plus Writer's Workshop pieces, several of you may spontaneously fall asleep. Do not attempt to read while operating heavy machinery.)
The stories do not have to be read in this order. If I was going to recommend that people begin at any given point... it would probably to start with 100% Move = 50% Fire and then go to A Total Eclipse Of The Fun, followed by the classic Any Sequence You Like. This just indicates where just about everything is on the timeline.
So with that boldfaced...
For the 'verse, each season of the show took place over the course of about one year, and each year can be considered to begin and end sometime in summer. (This isn't Hogwarts: everything does not clockwork-proceed into the sewers every June. There's a little flexibility.) Remember: for the show, the Summer Sun Celebration would be the longest day of the year -- and for Earth, that's the first day of summer. This ain't necessarily so for Equestria (and my version uses a lunar calendar), but let's pretend it is for a moment. So the series itself would begin in the last day or two of spring.
Why a year per season? To stretch things out. I wanted everypony to have time: they could get to know each other, have friendships deepen, work past sticking points. It also prevents a hyper-crowded calendar and trying to shuffle every last event around a mere 365 days while trying to figure out where everything fits. It turns the CMC's quest into something beyond ordinary futility and means Twilight didn't bring up the existence of a sibling for a really long time. Lull periods can exist while the town is reconstructed and everypony gets a chance to breathe. And it creates the idea that they all know each other by now -- while at the same time, there's still so much to discover.
So let's look at where things fit:
Preshowhistory
The deep, dark past: Twilight's school years, Pinkie's flight from the rock farm, and all the way back to the Discordian Era. Nothing's actually been set here yet as a full story. Two are tentatively planned, and one is a very long way off -- if it ever appears at all.
Season One
Extremely early summer: You all meet in the middle of a planetary extinction event...
Autumn: Permanent Record Starts at this point, but covers a couple of years, ending sometime after Babs visits Ponyville. Bobbie's first encounter with the CMC is when they're rehearsing for the talent show, so school is in session and the Crusade has been going for at least a few weeks.
Late winter: Blessing The first time Celestia's been thrown into the despair of helplessness since the Return. Just before equinox.
Early spring: 100% Move = 50% Fire This one is signposted all over the place. Fluttershy's modeling career is over, the Gala has yet to hit -- I have it as a late spring formal -- and Twilight's been in Ponyville for something around a year, or at least way too long for the Archives to still be putting up with her stuff remaining in the on-site apartment. Note that Snowflake hasn't moved into town yet (as it's pointed out that Fluttershy has nopony who can regularly cover for her): as he's present for the next story, figure him to arrive shortly after Return Day.
Season Two
Mid-autumn: On The Application Of Time And Motion Efficiency Studies To Initial Relationship Formation A critical Nightmare Night has passed. (Yes, in this continuity, Luna didn't reemerge into Ponyville for a long time.) However, Twilight's second Running Of The Leaves is a few weeks away. This may take place just a week or so after Luna's visit.
Spring: One Tenth-Bit Note the climate shift as nightfall approaches, along with Rarity and Luna having a good level of familiarity with each other.
Very late spring into summer: A Total Eclipse Of The Fun Actually spans the bridge between Season #2 and #3, beginning a few weeks before the Summer Sun Celebration and second annual Return Day, finishing a little less than a week after.
Season Three
Early summer: Princesses Can't Cook No more than a week or so past Luna & Celestia making that second agreement: everypony who was going to be rehired has been, Anise has effectively been kidnapped to the Solar staff, and Blending Stock is just starting as junior sous.
A Mark Of Appeal Starts about a week after the above.
Autumn: Stupid Direction-Face This one's pretty direct: it's fall, late summer brought a parasite infestation, and it's the year after Spike and Garble met. Year Three all the way.
Five Hundred Little Murders This one's a bit odd, timewise. There are points when it feels like a story of spring, and others when it turns into autumn. I'll keep it in the fall for now because it gives us a timeline for Killer's growth.
Luna's Lottery Lunacy Sometime after that year's Nightmare Night: the Gifted School is in session with no breaks on the horizon, which means Celestia can;'t even hope to send the students home for a couple of weeks.
Winter: The Hypocrisy Of Tolerance Flitter's had Killer for a while and he's been taken to Fluttershy for a checkup, while Hearth's Warming Eve has been over for a while.
From this point on, things start getting a little crowded.
Early spring: Sonic Rainbigot The press knows who the Bearers are: locally, that happened after the Cadance/Shining Armor wedding at the end of Season #2.
If Rainbow Dash can't sleep... About a week after the previous wraps up.
0G Network Coverage Following the events of Magic Duel, Celestia has taken custody of the Alicorn Amulet and Trixie is back on the road, under heavy probation. At this point, she's been exchanging notes on magic with Twilight for a while. A letter probably got launched from this...
Scootalift School is still in session, but the grass is green, the fields are blooming, and Scootaloo is completely fed up with her lack of flight progress. Might wind up overlapping somewhat with the below.
Late spring: A Confederacy Of Dunce Caps Starts one week before finals.
Early summer: Cutie Mark Crusaders Alpha Pack Leader We get the time of year in the first sentence.
Orange Is The New Blue Perhaps three weeks before Twilight's transformation. Tourist season is underway, the younglings are on the loose...
Dear Friend, Right around the ascension itself.
Season Four (The Local Version Only)
Late summer: Pinkie Pie vs. The Soufflé Pinkie directly notes that it's been two weeks since Twilight's change.
Triptych One week after the prior. Phases from late summer towards early autumn.
Snowflake Shoe-Hare Starts right after Chapter Four of the above, once Snowflake has been hired to watch the cottage during the latest mission.
The odd duck
Pony Up A Tree I'm not still not placing it exactly. However, it's an autumn story and the Bearers have been having their once-seasonal card game for some time. Given that Luna has become an occasional part of that gathering and they've cycled through everypony's home as a host site, we're at least a couple of years in. It will be tacked down -- eventually.
So that's the current order, subject to change as I recognize any stupid mistakes made. Also, I just scared off a lot of people. But that was inevitable, so I'll just politely wave and then wipe up the fear tracks.
And as long as I'm posting, here's today's secondary question: is it time to start breaking down the TVTropes page into separate story folders?
...yes, that mostly means me.
Thank you for spacing out the events of the first three seasons. I understand the initial argument of those who call for a single year, but it really breaks down when analyzed.
Also, folders would probably be advisable, yes.
2313354
The idea that all the seasons could take place in a single year is an abominable brainbug that never existed until people watched the S4 opening and didn't pay attention to what is actually said there.
So, uh. I'm basically completely agreeing with you and Estee, and just fuming over one of my personal fandom pet peeves.
Personally, I've always been sort of confused by the idea that they use OUR calendar and their year is as long as ours. Doing it this way means that we can have somepony remind somepony else that there's a leap-moon this year like what happens in the Hebrew and Chinese calendars.