Above the Valleys: From Derrybawn to Drumgoff on a Trail of Views, Rebels & Red Kites
There are some routes in Wicklow that feel like you’ve pedalled your way into Ireland’s ancient past from monastic masterpieces to our centuries of rebellion against English invaders and planters. My latest two wheeled adventure started in Laragh, always a busy village nestled in the centre of Wicklow, and it took me high above the world-famous Glendalough, across open mountain, down into the historic depths of Glenmalure, and up again to one of Ireland’s most iconic cycling landmarks. This one had everything: forest climbs, ridge views, a sighting of a red kite, and more than a little sweating!
Route Summary:
- Distance: 23 km
- Elevation Gain: 710 m
- Highest Point: 568 m above sea level
- Start/Finish: Laragh
- Terrain: Mixed surface – forest trails, mountain boardwalk, paved climbs, fast descent

The Derrybawn Loop – A Trail Above Time
I set off on the Derrybawn Loop, a well-marked hiking and biking trail that leaves from Laragh and climbs steeply through thick woodland above Glendalough’s monastic village. The climb wastes no time—it’s tough going, but the views are worth every crank of the pedals. I may be on an electric assisted bike but I still get the physical benefit of my efforts, with a little assistance when the going gets tough!
Soon breaks in the tree line appear, and you’re treated to breathtaking vistas of the Upper Lake, shimmering below like something out of a dream. The route sweeps around Derrybawn Mountain, with the Spink Ridge rising to the west—a dramatic walk in its own right and well worth the effort if you do visit Glenadalough on foot.
Eventually, the forest road gives way to a wooden boardwalk—floating above the heather and bog on the open mountain. At this point, I left the Derrybawn Loop behind and struck out toward the Miners Trail, which links Glendalough to Glenmalure. This is where the spin turns into something else entirely. First I had to lift the bike over a stile and then carefully walk the bike along the board walk – I’m not brave enough or foolish enough to try cycle on top of it! It’s a really steep descent after the boardwalk on a slippy gravelly mountain path.
Crossing to Glenmalure – Wicklow’s Rebel Heartland

The Miners Trail winds across open mountain and descends into the glacial expanse of Glenmalure, the longest glacial valley in Ireland. At 20km long, it’s a place that breathes history. Once the stronghold of the O’Byrne clan, Glenmalure was the site of fierce resistance to English rule, most famously the 1580 Battle of Glenmalure, where Fiach MacHugh O’Byrne and his followers delivered one of the heaviest defeats suffered by an English army in Ireland. He is immortalised in the ballad ‘Follow me up to Carlow’ The air to the song is reputed to have been played as a marching tune by the pipers of Fiach MacHugh O’Byrne:
Lift MacCahir Óg your face
Brooding over the old disgrace
That black Fitzwilliam stormed your place,
Drove you to the Fern
Grey said victory was sure
Soon the firebrand he'd secure;
Until he met at Glenmalure
With Fiach MacHugh O'Byrne.
Curse and swear Lord Kildare
Fiach will do what Fiach will dare
Now FitzWilliam, have a care
Fallen is your star, low
Up with halbert out with sword
On we'll go for by the Lord
Fiach MacHugh has given the word,
Follow me up to Carlow.
See the swords of Glen Imaal,
They're flashing over the English Pale
See all the children of the Gael,
Beneath O'Byrne's banners
Rooster of a fighting stock,
Would you let a Saxon cock
Crow out upon an Irish rock?
Fly up and teach him manners!
Curse and swear Lord Kildare
Fiach will do what Fiach will dare
Now FitzWilliam, have a care
Fallen is your star, low
Up with halbert out with sword
On we'll go for by the Lord
Fiach MacHugh has given the word,
Follow me up to Carlow.
From Tassagart to Clonmore,
There flows a stream of Saxon gore
O, great is Rory Óg O'More,
At sending the loons to Hades.
White is sick, Grey is fled,
Now for black FitzWilliam's head
We'll send it over dripping red,
To Queen Liza and her ladies.
As I descended toward Drumgoff Bridge, the landscape widened into that familiar U-shaped valley—a place both remote and full of presence. And as if scripted by nature itself, a red kite soared overhead, circling effortlessly on the thermals. These majestic birds of prey were reintroduced to Wicklow in recent years, and seeing one in flight is always a thrill—its forked tail and russet colouring unmistakable.

Crossing to Glenmalure – Wicklow’s Rebel Heartland

The Shay Elliott Climb – A Hill for the Heroes

From Drumgoff, the road pointed steeply upwards to the Shay Elliott Monument. This is one of Wicklow’s great cycling climbs—never too steep to break you, but long enough to test your grit. I never felt more like a cheat than I did at this point using an emtb! The monument honours Shay Elliott, the first Irish cyclist to wear the yellow jersey in the Tour de France, and the first to win a stage in all three Grand Tours.
The summit offers more than just lactic acid—it offers panoramic views back across Glenmalure, the mountains, and the winding ribbon of road you’ve just conquered.

Descent to Laragh – Back to Where It Began
From the monument, it’s all downhill—literally and joyfully. A winding, fast descent delivered me back toward Laragh after a really incredible route.
Laragh is a perfect base for outdoor adventures. With Glendalough just up the road—a place of saints, scholars, and silent lakes—it’s a hive of activity every weekend, especially when the sun shines!
Shout out to David Flanagan, who included the Derrybawn Loop in his fantastic guide book ‘Cycling in Ireland’, which is where I picked up this route from.























