Missing horses, amputated toes and a lonesome Wicklow bog — the story behind Art's Cross

With the help of Hugh O’Neill, 2nd Earl of Tyrone, the trio made a bid for freedom on the night of January 6, 1592. They scrambled down a chute with an improvised rope but, at this point, Art injured his foot in a fall. Despite the injury, they crossed the River Dodder and escaped beyond the walls of what was then a tiny city. The plan was that horses would be provided to facilitate their escape. These failed to materialise, so they continued on foot while hampered by Art’s injury. Under the guidance of Turlough O’Hagen, who had been sent by Hugh O’Neill to facilitate the escape, they headed southwest through Harold’s Cross, Kimmage, Templeogue, Firhouse, and Ballyboden and were soon outside the area where English law applied.

Somewhere along the way, Henry became detached from the others and made his own way back to Ulster. Art and Red Hugh continued in a snowstorm through the western foothills of the Wicklow Mountains, thus avoiding the wildest and most unforgiving terrain that lies around the Sally Gap. Exactly how they journeyed is impossible to say, but they did successfully reach the Wicklow Gap which, considering the prevailing conditions, was in itself a considerable achievement. According to tradition, they then headed south through Glenreemore Valley, but on the unforgiving slopes of Conavalla Mountain, found it impossible to go further.

O’Hagen was dispatched to Ballinacor Castle, Glenmalure to seek help from the Irish chieftain Fiach MacHugh O’Byrne. He immediately sent men with food and beer, but when they reached the Ulster princes, both were unconscious in the snow. Art never regained consciousness, and his remains now repose somewhere amid the lonesome bogs of the Wicklow uplands.O’Donnell rallied, however — he ate some food, and then recovered sufficiently to make it down to Glenmalure. Unsurprisingly, it took him a considerable period to recover, by which time he had had his big toes amputated due to frostbite. Afterward, he journeyed to Ulster, where at the age of 20, he stood on the Rock of Doone, (the traditional inauguration stone for O’Donnell clan) and was proclaimed as The O’Donnell, Prince of Tyrconnell. Now an implacable enemy of English rule, O’Donnell nursed a deeply felt sense of grievance which made him a most dangerous adversary.

Meanwhile, Hugh O’Neill — who had until recently co-operated with English rule — had a change of heart. He decided to ally himself with the Catholic Counter-Reformation, which was aimed at halting the advance of Protestantism in Europe. Renouncing the Earldom of Tyrone, he reverted to the ancient Gaelic title of The O’Neill and became the leading exponent of Catholicism in Ireland.

Having now crossed his Rubicon, O’Neill immediately formed an alliance with O’Donnell that was aimed at eliminating English rule from Ireland. Initially, what later became known as the Nine Years War went well for the Ulster rebels as they repulsed many attempts to invade their territories. O’Neill and O’Donnell then decided to make an appeal for direct military intervention from Philip III of Spain.

When the smaller-than-expected Spanish force eventually arrived at Kinsale, County Cork, Mountjoy, the English Lord Deputy in Ireland, laid siege to them. O’Neill and O’Donnell then marched south intending to trap Mountjoy’s army between the Irish and Spanish.

Surprised by a sudden counterattack, as they prepared an assault on the English, the Irish chieftains were routed and retreated forlornly to Ulster, while the Spanish surrendered and were returned home. Unable, perhaps, to cope with the magnitude of the defeat, O’Donnell left Ireland almost immediately and sailed to Galicia, Spain with the promise that he would return with a large army. Journeying onwards to the royal palace at Valladolid to try to persuade Philip III to intervene in Ireland once again, he died unexpectedly on September 10, 1602.

His memory lives on, however. It is preserved by a large statue in his native Donegal; while a walking trail in County Tipperary (The Red Hugh Loop) recalls his march to Kinsale. Finally, he is commemorated annually by the Art O’Neill challenge. This, continually oversubscribed event takes place each January. It is then that 200 ultra-runners and walkers plunge out at midnight to follow 55km in the footsteps of Art and Hugh on the long and exhausting traverse from Dublin Castle to Glenmalure.

• John G O'Dwyer's book Wild Stories from the Irish Uplands contains the full account of the escape of the Ulster princes