In the books
Ashford is the site of two important events in the history of the Seven Kingdoms. In 209 AL Ashford was the site of a tournament where the much-storied knight Ser Duncan the Tall first began his rise to fame and where he first met his even more famous companion, Egg. Prince Baelor 'Breakspear' Targaryen, the king's heir, was also accidentally killed during this tourney, changing the future history of the Seven Kingdoms.
In 281 AL, during Robert's Rebellion, Ashford was the site of a major battle and Robert Baratheon's only notable defeat. The army of House Tyrell was advancing towards the Stormlands with the intention of destroying Robert's army and taking Storm's End. Robert elected to fight a field battle rather than withstand siege and intercepted the Tyrell army near Ashford. Robert attacked the Tyrell vanguard (which Robert's army outnumbered at a local level, since the bulk of the Tyrell army had not yet arrived). However, Lord Randyll Tarly, commanding the Tyrell van, withstood the attack and drove the Baratheon army from the field. Robert's army was defeated, but managed to withdraw in good order northwards towards the Riverlands. The Tyrell army was commanded to march on to Storm's End (held by Stannis Baratheon) and besiege it rather than pursue Robert. This proved unwise, as Robert was able to combine his army with those of the Starks, Arryns and Tullys, enabling him to ultimately triumph in the war.
- Ashford at A Wiki of Ice and Fire (spoilers from the books).
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