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All of the following is tentative and subject to change
~1000 years ago - Twin alicorn princesses are born on Equestria. Their innate power and goodness is so great that the Dark Forces that plague the land retreat before it.
Roughly 17 years after that, several thousand light years away, another pony planet known as Argonia is invaded by a mysterious and hostile force. The invaders, led by a horrific pony named Zoda, lay waste to the planet and the population when the Argonians refuse to surrender to their rule. The Argonians manage to put un enough of a fight against the invaders that a sizable portion of their population is able to flee the planet, including a stasis pod containing the Argonians' own young alicorn princess and six of her closest friends.
~950 years ago - An Argonian stasis pod is mistaken to be a meteor as it crashes into the ruins of an ancient pony civilization in the South Islands.
~900 years ago - The Dark Forces begin to tire of hiding in remote caves and start to organize into armies and attack cities all over Equestria. Celestia, the more proactive of the princesses, decides to form an army to fight back. A pony known as Gallant Garion becomes one of the first generals of the army and leads them to many victories over the Dark Forces.
~850 year ago - During one particular engagement that Celestia herself was present for, the princess is struck with an unknown form of dark energy. She appears to be unaffected, and the incident is written off as unimportant.
Gallant Garion willingly volunteers for a magical procedure to make him an immortal servant in Celestia's army. However, the process goes awry and the villainous Simmer escapes into the wilds of Equestria.
~850 years ago to 20 years ago - Celestia gradually becomes more agressive and tempermental as the undetected taint from the darkness she was struck with influences her mind so gradually as to be unnoticable. As her temper worsens, only her sister Luna is able to stave of the worst parts of her personality.
Argonian Space Pony refugees arrive on the planet sporadically and are absorbed into the greater population.
Zoda hunts down the Argonian refugees across space, not knowing that political maneuvering (aka backstabbing) and subversive rebel movements are gradually eroding his existing galactic empire.
~500 years ago - A group of settlers in the northern mountains find a ship they name the Ark of Yamato frozen solid in a mountain lake. The lake remains solidly frozen for centuries.
~250 years ago: Due to a diplomatic breakdown whose root is lost to history, the griffons went to war with Equestria seeking to claim a section of the border (now known as the Hipogrif March). Outnumbered and facing pony magic, they still attacked. After the initial shock, the royal army pushed them back, forcing a treaty that lead to the current semi-autonomous region of the "Silver-Feather Highlands."
~110 years ago - An innately amoral pony named Xykon is born. He quickly kills his own family at a young age and joins the Dark Forces for a few decades before striking out independently.
~30 years ago - Xykon transforms himself into a skeletal abomination using forbidden magics. He bigins a plot to steal the powers of the princesses themselves.
20 years ago - Organized Dark Forces armies show up claiming alliegance to an unknown individual they call 'Iron Hoof'.
Celestia's temper finally reaches levels where even Luna can no longer calm her sister.
13 years ago: The Mountian Moose king, Jotun the Red signs a peace treaty with Equestria.
10 years ago - Celestia imprisons Luna in the moon after her sister was supposedly taken over by the Dark Forces and transformed into 'Nightmare Moon'.
The Rime Moose conquered Moosegard and suddenly attacked Equestria. The invasion was repelled by the Equestrian military in a month but took heavy losses.
10-5 years ago - It is revealed that 'Iron Hoof' is actually an evil split personality of Celestia that has become dominant in recent years.
Celestia begins a tyrranical reign over Equestria under a sun that never sets, and a summer that never ends. She brutally quelches any resistance with either the Equestrian army, or an army of monsters under her control.
A division in an old clan of Unicorn pyromancers throws nearly every fire-using pony in Equestria, including the entire Fire Pony race, into a bloody civil war.
During The Summer, a large section of the griffon population wished to rebel against their blood ally ponies. A coalition of the reformers and loyalists fought them, eventually destroying the rebel army by trapping it between a small Equestrian force and itself.
A young pony named Twilight discovers that 'Nightmare Moon' never truly existed and plots to release Luna.
5 years ago - Luna escapes her prison thanks to Twilight. Together, they manage to best Celestia and imprison her in the sun. At the same time, they manage to dispel the evil personality of 'Iron Hoof' and free Celestia from direct influence by the Dark Forces.
Luna, loving her sister very much, allows Celestia to contact ponies outside her prison. However, Celestia's personality is still highly aggressive and she and Luna get into frequent arguments over how Equestria should be run.
Unable to reconcile their differences, and legitimately fearing that her sister might suffer a relapse into 'Iron Hoof', Luna does not ever set Celestia free. Celestia understands this position to a degree, but she feels that Luna is much too soft and forgiving to do what needs to be done to combat the Dark Forces which grow ever stronger.
3 years ago - Zoda finally locates the escape pod that held the Argonian Princess in the South Islands and lands his flagship. He kidnaps a local archaeologist and has him decipher the instructions to bring the ponies in stasis out. The kidnapped pony's nephew, Mike, a Sea Pony named Echo Wave, and a wandering bard named Eric, band together to locate and rescue Mike's uncle, and then the Space Ponies in stasis, and hand Zoda his first military defeat in over a millenium. In the process, they destroy Zoda's flagship and strand the alien conqueror on Equestria with no way to contact his extraequestrian armies which also never come looking for him.
Mike is able to free the Space Ponies from stasis and the Argonian Princess Mica finally awakens after nearly a thousand years of sleep
Mike, Mica, Echo, and Eric are later joined by two other ponies, Shutter Shade and a pure white adult Blank Flank called Ammy. Together they call themselves the Starlight Six.
The 40-day revolt. The two remaining griffon factions fight to see their vision of the future of the Highlands come to be. With the traditionalists victorious, the reformers were dealt with.
2 years ago - Following a blood oath from his father, Roy forms a band known as the Order of the Stick to hunt down and destroy Xykon.
1 year ago - The Great Eclipse occurs.
Despite most science ponies saying that most of Equestria will only be able to see a partial eclipse, everypony views a full eclipse that then plunges the world into darkness. For several minutes, many ponies are claiming everything from Celestia turning the sun black from within to Luna finally showing her 'true evil colors' to the Dark Forces being victorious. Then the sun comes out and the shadows are banished.
The official statement from Luna is that the event was due to a horrible weapon of the Dark Forces that was so powerful even the Dark Forces rightly feared it. Both she and her imprisoned sister present medals to a band known as the Starlight Six which they publicly credit with this weapon's defeat. Most ponies believe this story at face value, and within twenty four hours this previously unknown weapon has a dozen different foreboding titles/nicknames.
The Starlight Six publicly disbands after they are awarded medals by both princesses. Oddly, a Pony Fly named Issun is among their ranks at the time instead of a now mysteriously missing Ammy.
6 months ago - Xykon finally puts his plan to drain the princesses into action. Targeting the imprisoned Celestia, he is able to begin siphoning her powers without breaking or entering her prison in a process that would have killed Celestia had it succeeded. However, he is defeated and destroyed by the Order of the Stick at the cost of the lives of two of their members, saving Celestia's life. Thankfully, the details of the process Xykon developed die with him.
The Order is presented with both the Lunar and Solar Medals of Honor, including posthumous honors to their fallen members, for their defeat of Xykon.
Zoda's name begins to circulate across Equestria as a new powerful commander of the Dark Forces' armies.
Spoiler
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All of the following is tentative and subject to change
*~2000 years ago - The Dark Ages ended with the formation of Equestria.
*~1200 years ago - A chaotic spirit by the name of Discord seizes power in Equestria and begins a long reign of terror. Around this time, the group known as Dark Forces was recorded to have started their activities.
~1000 years ago - Twin alicorn princesses are born on Equestria. With their innate powers, together they banished Discord to a statue and restored order to Equestria. The Dark Forces retreats to their hideouts as their patron ruler was removed from power.
~900 years ago - The Dark Forces begin to tire of hiding in remote caves and start to organize into armies and attack cities all over Equestria. Celestia, the more proactive of the princesses, decides to form an army to fight back. A pony known as Gallant Garion becomes one of the first generals of the army and leads them to many victories over the Dark Forces.
~850 year ago - During one particular engagement that Celestia herself was present for, the princess is struck with an unknown form of dark energy. She appears to be unaffected, and the incident is written off as unimportant.
Gallant Garion willingly volunteers for a magical procedure to make him an immortal servant in Celestia's army. However, the process goes awry and the villainous Simmer escapes into the wilds of Equestria.
Celestia gradually becomes more agressive and tempermental as the undetected taint from the darkness she was struck with influences her mind so gradually as to be unnoticable. As her temper worsens, only her sister Luna is able to stave of the worst parts of her personality.
*~500 years ago - An abandoned space ship was found in the frozen wastes of the Great Tundra. Enterprising ponies immediately begin studying and reverse-engineering the technology of the ship, fuelling a technology boom which was to last for decades. It is said Princess Luna herself encourages such activities.
*~400 years ago - The zebra nation of Zebrica went into isolation, permitting no outsiders to enter their territory. No official reason was ever given.
~250 years ago: Due to a diplomatic breakdown whose root is lost to history, the griffons of The Eyrie went to war with Equestria seeking to claim a section of the border (now known as the Hipogrif March). Outnumbered and facing pony magic, they still attacked. After the initial shock, the royal army pushed them back, forcing a treaty that lead to the current semi-autonomous region of the "Silver-Feather Highlands."
*~100 years ago - Rumours of alien ponies mingling with the locals gain popularity. No evidence was found to substantiate the rumours, but sightings are often reported.
30 years ago - Organized Dark Forces armies show up claiming alliegance to an unknown individual they call 'Iron Hoof'. Although they pose a severe threat to the border regions, the Equestrian Army manages to keep them in check.
Celestia's temper finally reaches levels where even Luna can no longer calm her sister.
16 years ago: The Mountian Moose king, Jotun the Red signs a peace treaty with Equestria.
10 years ago - Celestia imprisons Luna in the moon after her sister was supposedly taken over by the Dark Forces and transformed into 'Nightmare Moon'.
The Rime Moose conquers Moosegard, then turn their attention towards Equestria. The invasion was repelled successfully by the Equestrian military with heavy losses.
*9 years ago - It is revealed that 'Iron Hoof' is actually an evil split personality of Celestia that has become dominant in recent years.
Celestia begins a tyrranical reign over Equestria under a sun that never sets, and a summer that never ends. She brutally quelches any resistance with either the Equestrian army, or an army of monsters under her control. Civil war erupts as ponies align themselves with either Iron Hoof or the banished Night Goddess.
8 years ago - A division in an old clan of Unicorn pyromancers throws nearly every fire-using pony in Equestria, including the entire Fire Pony race, into a bloody civil war.
*Valhalla was destroyed in an epic display of power by Celestia. The remaining rebellious northern cities soon surrender.
6 years ago - A large section of the griffon population wished to rebel against their blood ally ponies. A coalition of the reformers and loyalists fought them, eventually destroying the rebel army by trapping it between a small Equestrian force and itself.
A young pony named Twilight Sparkle from Ponyville discovers that 'Nightmare Moon' never truly existed and plots to release Luna.
*5 years ago - Luna escapes her prison thanks to Twilight Sparkle and her friends. Newly invigorated, she rallies her loyal supporters and begin the rebellion anew.
Together with the Elements of Harmony, they manage to best Celestia and imprison her in the sun. At the same time, they manage to dispel the evil personality of 'Iron Hoof' and free Celestia from direct influence by the Dark Forces. It was not without cost however, as the town of Ponyville was badly damaged in the fight. Armies under the Dark Forces melt away amidst the chaos.
Luna, loving her sister very much, allows Celestia to contact ponies outside her prison. However, Celestia's personality is still highly aggressive and she and Luna get into frequent arguments over how Equestria should be run.
Unable to reconcile their differences, and legitimately fearing that her sister might suffer a relapse into 'Iron Hoof', Luna does not ever set Celestia free. Celestia understands this position to a degree, but she feels that Luna is much too soft and forgiving to do what needs to be done to combat the Dark Forces which grow ever stronger.
*The New Lunar Republic was declared to replace the former Kingdom of Equestria, with the former Prince Blueblood being the first prime minister. Many ponies remains loyal to Celestia and war erupts anew as the two sides clash. However, with Celestia's imprisonment, the resistance was disorganised and mostly limited to local rebellions.
3 years ago - The 40-Day Revolt. The two remaining griffon factions fight to see their vision of the future of the Highlands come to be. With the traditionalists victorious, the reformers were dealt with. (Needs clarification. Who are the traditionalists and reformers?)
*2 years ago - Equestria was finally declared to be united by Blueblood. However, this is an uneasy peace, with rumours of Dark Forces gathering their armies again and the renewed threat of invasion by the belligerent Rime Moose and griffons.
1 year ago - The Great Eclipse occurs.
Despite most science ponies saying that most of Equestria will only be able to see a partial eclipse, everypony views a full eclipse that then plunges the world into darkness. For several minutes, many ponies are claiming everything from Celestia turning the sun black from within to Luna finally showing her 'true evil colors' to the Dark Forces being victorious. Then the sun comes out and the shadows are banished. The official statement from Luna is that the event was due to a horrible weapon of the Dark Forces that was so powerful even the Dark Forces rightly feared it.
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