Rebels, Ridges & Back Roads. Two glorious Evening Spins in the Garden of Ireland.
There’s something special about cycling in the evening light—especially in County Wicklow, where every bend in the road reveals a piece of history or a sweep of mountain beauty. Over two recent evenings, I explored two routes not far from each other—each steeped in legend, rebellion, and raw, rugged charm. If you ever doubted that the past is alive in Wicklow, these spins might just convince you otherwise.
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Evening 1: Knockananna, The Billies, and the Ghosts of 1798
My first loop began in Knockananna, a village on the border with Carlow —tucked into the hills and humming with local pride. The road led me high up into Askanagap, home of Ballymanus GAA club, also fondly known as The Billies, a tribute to local 1798 rebel Billy Byrne.
Byrne wasn’t just a namesake—he was a key figure in the rebellion, fighting at Arklow, Mount Pleasant, Kilcavan, and finally Vinegar Hill in Enniscorthy.
His tragic end is remembered in memorial plaque in front of the Club. Captured in 1799, he was tried in Wicklow town on the evidence of four paid informers—Dixon, Doyle, Davis, and Bid Doolin. As the story goes, he was playing handball in the prison yard when summoned to his execution on Gallows Hill. His brother had raced from Dublin with a reprieve, only to arrive 15 minutes too late.
As I rode back toward Knockananna, the road brought me to the hauntingly beautiful Rosahane Graveyard, tucked away on a quiet hillside. Two young deer darted across the road below me—one of those small, unforgettable moments that make evening cycling in Wicklow so special.
Evening 2: Aughavannagh, Glenmalure & the Shadow of Fiach MacHugh
The second evening took me deeper into the mountains, starting from Aughavannagh, a peaceful spot nestled in the heart of Wicklow. My route looped around Ballinacor Mountain, dropped down into Greenan, and then swung left into the wide, silent majesty of Glenmalure.
This is no ordinary valley—it’s a 20km-long glacial trench, once the stronghold of the O’Byrne Clan. In 1274, they ambushed a Crown force here. More famously, in 1580, Fiach MacHugh O’Byrne crushed an English army in the Battle of Glenmalure, inflicting between 500 and 1,000 casualties in what remains one of the most decisive rebel victories in Irish history. I can only imagine how remote this place was before out modern network of roads.
At the entrance to the valley stands a huge boulder: one face honours Fiach MacHugh; the other commemorates Michael Dwyer, another 1798 rebel of legend and a native of nearby Glen of Imaal. It’s a stark reminder that these quiet roads once echoed with battle cries and coercion of the native population.
From there, a tough climb over Drumgoff brought me to a stunning final descent—one of those long, freewheeling glides that make every climb worth it—back into Aughavannagh as the evening light melted into the hills.
Both routes were rich in scenery and history. From rebel battlegrounds to glacial valleys, ancient graveyards to whispering forests, these were two great evening rides that inspired the legs and the soul!
The weather was perfect. The roads were quiet. And the hills and the locals—well, they haven’t forgotten.
