- Not known to frequent tourney's, Aleister was a relative unknown outside of Hollyholt. His first appearance to many of those in the Riverlands was in January of 289 when he was sent from Hollyholt to the township of Stonebridge with twenty knights, twenty squires and twenty men-at-arms, to answer the muster against the Ironborn that had invaded their lands.
- Participated in the battles that broke the siege of Terrick's Roost, escaping unscathed throughout each.
- During the final battle of Seagard, Aleister was in command of the armies at the Waterfront, tasked with cutting off the Ironborn's retreat. During the battle, he engaged Lord Volmark in single combat, critically wounding the Ironborn Lord before being felled by a massive blow to his head from Volmark's two-handed axe.
- As a result of his injury, Aleister spent a week in a state of a high fever and when it came to finally break, it's been said that the Lord was changed as a result.
- In February of 289, under the authorization of Lord Ser Keegan Charlton, Aleister formed a Cadet Branch of House Charlton under the name House Charlton of Highfield. Upon departing for the Iron Isles, Aleister entrusted Ceinlys Erenford to oversee the developing of the land.
- Returned from the Iron Isles in April 289.
- By June of 289, Highfield's township had been well established
- In August of 289, Lord Tully confirmed Aleister as the Knight of Highfield and officially awarded the lands to him.
- In October of 289, following the severing of the vassalage of House Charlton of Hollyholt to House Frey, House Charlton of Highfield severed its ties with its former liege, abandoning the Charlton name and taking the name Ashwood. House Ashwood is sworn in fealty and service to House Frey.