The Art O'Neill Challenge is a unique event in the Irish outdoor scene, organised by, and solely for the benefit of, Dublin & Wicklow Mountain Rescue Team. Its 53km route retraces a historic escape from Dublin Castle that happened on January 6th, 1592. That night, Art O'Neill, his brother Henry, and Red Hugh O'Donnell broke out of the Castle and made for Glenmalure, to safety. On a freezing night the three made their way on foot and without the benefit of winter coats, having had to leave them in their cells. Henry and Hugh were both made it to safety but sadly Art, for whom the Challenge is named, succumbed to hypothermia along the way.

People have been commemorating the escape for many years, but in 2006 the Challenge became an organised event. Initially, the Art O'Neill Challenge was a fundraiser for rugby player Stuart Mangan. It then became a commercially organised event, during which time it grew, owing to the hard work of Declan Cunningham and Gearoid Towey, into the event it is today. In 2018, organisation of the event passed to Dublin & Wicklow Mountain Rescue Team, and it now serves as a major fundraiser for the team.

The Challenge follows one route, but includes three options to participants: trek, hybrid, and ultra. Trek is for the traditionalists, walking all the way. Hybrid is for those who are comfortable running on road, but prefer to walk the hills. If a self-guided ultramarathon is what you're after, Ultra is for you. The route is on road for the first 30km, after which you'll find checkpoint one, in Ballynultagh Wood. From checkpoint one, the route heads over Billy Byrne's Gap and down to checkpoint two, near Ballinagee Bridge. After checkpoint two, the route passes Art's Cross before heading down Table Track to finish in Baravore.

The event is run and staffed by members of Dublin & Wicklow Mountain Rescue Team, with the help of volunteers very generously donating their time. Safety and rescue cover is provided by rescue team members, with guiding also, in the main, provided by mountain rescuers. Checkpoints one and two offer a place to rest and refuel by the fire. Checkpoint one is also where participants will find their drop-bag, allowing access to a change of clothes, or whatever will make the last 23km of open hillside more comfortable. At Baravore, participants will be reunited with their drop-bags, and bus transfers are provided back to Dublin. The Art O'Neill Challenge provides much-needed funds to keep Dublin & Wicklow Mountain Rescue Team operational, allowing the team's volunteers to maintain its 24/7 emergency response to those in need.

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