Twenty long years come and go, allowing Princess Twilight and company to grow apart chasing down their own dreams. Having attained a time of peace in all of Equestria once more, Celestia feels that her faithful students have experienced full enough lives to be prepared for one final task; the founding of a kingdom they can all call their own.

Placed on the shoulders of Twilight Sparkle, the young princess accepts the mission and rounds up her friends to share in one last adventure together. A caravan of settlers and a small collection of royal guards are placed under Princess Twilight's charge, and the Mane Six must forage on to the destination of their new home.

After initiating what seemed like the simplest of tasks, Twilight and company begin to experience the hardships of both the journey, and the strain that exists between their once strong relationship. A dark, new shadow now looms over the would-be founders, patiently biding it's time to exact bitter-sweet revenge on the band of ponies for a long-forgotten wrong. Can the Mane Six get it together before a nightmare descends upon them, or will the trials of time prove too great to overcome?