The town has whitewashed houses with thatched roofs. Nearby Ashford Castle is built in the shape of a triangle, with round towers thirty feet tall at each point. Between the towers run thick crenellated walls.
In 209 ᴀᴄ the Ashford tourney was held in Ashford Meadow south of the Cockleswent. After being killed in a trial of seven, Baelor Targaryen, Prince of Dragonstone, was cremated in the yard of Ashford Castle.
The Battle of Ashford in 282 ᴀᴄ was the only defeat of Lord Robert Baratheon during Robert's Rebellion. Commanding the vanguard, Lord Randyll Tarly forced Robert to retreat before Lord Mace Tyrell's main force arrived. Despite Randyll's leadership, Mace took credit for the indecisive victory.