Ser Harold is one of late Lord Ramsey Charlton's sons, a younger brother of the current Lord Keegan. As an expendable spare son, he was raised to remember that his duty was always to support his older brother, and curtail his own ambitions. If he ever begrudged that fate, he's never let it show. Instead he has always been a steadfast supporter of his family, and their overlords the Freys. In wartime he's an old veteran who has few scruples, while in peace he's generally known as an able and fair man. He's more likely to offer advise than lead himself, but wont shy away from necessity either. All in all he tends to come off as a grizzled and loyal veteran, helpful to the younger generation when asked. In his brother's name he holds some lands, managing a couple of small villages, and when great events doesn't call him out it's often been there he's spent his time. Glorified land-manager though the job might be, he's taken pride to seeing things grow and prospere, for all that he's a warrior at heart. Kellen is a couple of hours from Hollyholt, by the foothills of the Mountains of the Moon.
At the age of seven he was fostered out to the Darrys of Darry. Fierce rivals of the Freys, officially he was there to defuse relations between the Darrys and the Freys' chief vassals, but reality was less pleasant. His father wanted one of his sons to know the Darry lands and fortifications as well as his own in case hostilities broke out. And should hostilities come while he was there, then he was an expendable hostage that wouldn't be missed too much. Despite his underhanded mission Harold grew fond of the Darrys.
It was at Darry he first distinguished himself: a mere fifteen and charging a pair of brigands attempting to steal one of the Lady's horses. He killed one and wounded the other, who he brought back to face the Lord's justice. He squired and was later knighted under Ser Raymund Darry, brother of the famous Ser Jonothor Darry of the Kingsguard, and of Ser Willem Darrey, Master at Arms of the Red Keep. He had the honor of being instructed by the same arms master at Darry who turned out a Kingsguard. He also had the honor of having been beaten roundly by the same Kingsguard after a youthful boast of his sword skills, an event that taught him a bit of humility.
He was knighted at the age of seventeen, in what was later known as the Battle of the Honeyfields. In reality it was less of a battle and more of a minor skirmish; hilltribe raiders come down to wreck havoc and steal what could be stolen. Ser Raymund's horse went down in the first charge, his leg crushed beneath him and helpless, and enemies closing. It was Harold who kept them at bay, dodging and parrying, taking injuries twice, far too occupied to even consider attemping killing blows of his own. Once the foot turned the tide, he was solemnly rewarded for his valor.
By the time of Robert's rebellion he was already an established and battle hardened knight of thirty. He didn't participate in the Battle of the Trident, held back by the Freys, but he did ride with Eddard Stark for King's Landing. Later he participated in a puntive raid against the Darrys, who had refused to yield to the very end - the choice that reduced a once proud lordly house to their current status of landed knighthood - where he crossed swords with old friends, showing no mercy.
He fought with his House during the Greyjoy rebellion.
Though he's not known for being a particularly prolific tourney knight, he was at the Tourney at Harrenhal. He was unhorsed on the very first day. He also faught in the seven sided melee, where he acquitted himself well.
He is a man heading into his fourties. His once brown hair is turning towards the gray, and there are similar seams of colour touching his beard. He has a proud warrior's posture and stands tall at about 6'3'', with a solidly athletic build. His height sometimes gives the illusion of leanness, even if he's got shoulders made to swing a sword and bludgeon an armoured opponent to death. From within a face starting to line, flint gray eyes (with just a hint of blue) shine with both alertness and intelligence, and the confidence earned by blood and accomplishment. There's a visible scar on his neck, running around the left side as if someone once tried to cut his throat, but couldn't quite get the job done, and another hinted at along his strong jaw, running beneath his beard up towards his bottom lip.
Lord Ser Keegan Charlton, Lord of Hollyholt, eldest brother.
Lady Keera Charlton nee Haigh, Lady of Hollyholt, sister-in-law.
Young Lord Ser Andrey Charlton, Heir to Hollyholt, nephew.
Lady Alys Charlton, niece.
Ser Jon Ashwood, older brother.
Lady Kaytlin Ashwood, sister-in-law.
Lord Ser Aleister Ashwood, Lord of Highfield, nephew.
Lady Cherise Charlton nee Westerling, Lady of Highfield, niece-by-law. Annulled.
Young Lord Aeric Ashwood, Heir to Highfield, grand-nephew. Dead
Lady Aeliana Ashwood, favorite niece.
Ser Bastien Ashwood, nephew.
Robben Ashwood, nephew.
Ser Saethwyr Ashwood, nephew.