Here is the full list of all 28 Massive Chalice achievements.
Survived 300 years (Reached year 301)
Defeated an enemy from the past
Killed 5 or more enemies with a drunk hero in one tactical battle
Survived 150 years (Reached year 151)
Adopted multiple children into the same Keep
Kill 4 or more enemies with one attack
Killed an enemy with a Burst Bush
Survived 50 years (Reached year 51)
Received your first Relic
Appointed a Sagewright
Your first hero came of age
Appointed a Standard
The first baby was born
Arranged your first Marriage
Defended your first Keep
Completed the game on Normal Difficulty
Completed the game on Hard Difficulty
Completed the game on Brütal Difficulty
Completed an IRON game (any Difficulty)
Completed an IRON game (Brütal Difficulty)
Built a building in every Region
Beat a tactical battle where every hero is over 60 years old
Beat a tactical battle without taking any damage
Progressed a Relic to its maximum level
Deployed a Vanguard with only Cadence Weapons, Armor, and Items
Deployed a Vanguard of 5 different classes
Killed 50 or more enemies with one hero
Took at least 3 of your 5 initial Vanguard Bloodlines all the way to the Final Battle