Run for the Hills - Frank McNally on a modern re-enactment of Dublin Castle’s great escape

The Art O’Neill Challenge

The great Phil Lynott, about whom I was writing only last week (Diary, January 11th) is sometimes unfairly included in “worst lyric” lists for his prediction: “Tonight there’s gonna be a jailbreak/Somewhere in this town.”

Sarcastic commentators, purporting to advise him on the likely whereabouts of the break-out, tend to say: “Try the jail.” But as Lynott well knew, the fugitives could be using a tunnel, or even a sewer pipe like the man in the Shawshank Redemption. They could emerge anywhere.

Even so, acting on intelligence last Friday night, I positioned myself directly outside the main gate of Dublin Castle, from which I had reason to believe there was to be an imminent mass escape.

This although, as of 10.50pm, the gate was firmly closed. Then a few minutes later, sure enough, a man inside opened it. And at precisely 11pm, as my sources had indicated, 100 or so inmates suddenly scarpered from the castle courtyard and out through the entrance.


There they turned sharp left up Castle Street and disappeared in the direction of the Wicklow Mountains, with a Jeep – lights flashing – in hot pursuit.

I say they “scarpered”, but in fact the participants were clearly pacing themselves, knowing that a tough 60km route lay ahead. For although they were re-enacting the 1592 escape of the O’Neill Brothers – Art and Henry – and Red Hugh O’Donnell, there was only so much authenticity anyone wanted.

The annual commemoration is called the Art O’Neill Challenge because the original Art died en route, after falling asleep in the mountain snow before he could reach the safety of Fiach MacHugh Byrne’s fort in Glenmalure.

O’Donnell did make it, eventually, but lost both big toes to frostbite. Only Henry escaped fully intact. And when he returned to his native Ulster, the province’s most powerful chieftain Hugh O’Neill – who had probably helped spring the trio – took the trouble of locking him up again.

The O’Neill brothers were not necessarily allies of Hugh: on the contrary, they were potential rivals. Getting them out of mischievous English hands may have been more of a defensive strategy than a desire for their freedom.

Use of high-performance clothing, footwear, and nutrition aside, the modern re-enactment takes a few liberties with the 1592 event. For one thing, that happened on the Feast of the Epiphany – January 6th. This year’s version was a week later.

As well as the main challenge, there is also now a shorter, 25km race – the Art O’Neill pursuit – inspired by the original chase, which gave up on the safe side of the mountains. Amusingly, this started an hour earlier than Friday night’s main race, so that in theory at least, the escapees could have caught the pursuers.

Another key difference in the re-enactment, luckily for participants, is that it starts at ground level, not at the top of the Record Tower, where the real prisoners were kept. This also means the re-enactors don’t have to go through the garderobe (a hole-in-the-wall toilet).

The indignity of that apart, it was the descent that may have sealed Art O’Neill’s doom. Overweight from his time in jail, he injured himself during a heavy landing. That and scarce clothing left the escapees at the mercy of extreme weather. They may have had to shed some of what they wore to squeeze through the garderobe chute, or to use for the improvised rope.

One more crucial divergence between the historic event and re-enactment is that, providing some prior justification for Phil Lynott, the original fugitives escaped via the river Poddle, which then as now runs under Dublin Castle and provided plumbing for the garderobe.

Although only a minor waterway, the Poddle has long been of great strategic importance. Running under the seat of English rule, it had subversive potential long after the defeat of Gaelic Ireland. During the Fenian uprising of 1867, authorities saw fit to put a locked grill on the tunnel by which it joins the Liffey, lest a raft of explosives be floated up the culvert.

Getting back to the events of 1592, O’Neill and O’Donnell are said to have endured “a night and a day of agony” even before reaching the dangerous incline into Glenmalure Valley, from where they had to send for help and where O’Neill died.

The 2023 re-enactors fared better, thanks in part to the Dublin & Wicklow Mountain Rescue Team, which oversaw their efforts (and supplied the chasing Jeep). The winners were safely in Glenamalure well before dawn. First man home was Fabio Baltieri in just under six hours and 53 minutes, while the first woman was Ellen Vitting in eight hours, 26 minutes and 49 seconds.