Most of this stretch of the trail is on forest roads. From the Monastic City at Glendalough, the Way follows the Green Road towards the Upper Lake. It passes through an area of native woodland made up of oak, holly, birch, and rowan. Ascending from the Upper Lake, the trail reaches Poulanass Waterfall which, over millennia, has cut a narrow gorge through the slate rock and borne millions of tonnes of rock, sand and mud into Glendalough, dividing what was originally one lake into the two seen today. The trail continues its ascent through forest before emerging onto the saddle between Mullacor and Lugduff mountains at Borenacrow. The Borenacrow route between Glendalough and Glenmalure dates back to ancient times and there is a local tradition that Saint Kevin travelled this way to celebrate Mass in Glenmalure. The view ahead looks across the Glenmalure valley at Fraughan Rock Glen and Lugnaquilla, Wicklow's highest mountain at . The Way then begins a long descent into Glenmalure, the longest glacial valley in Ireland and Great Britain. Along the way the trail passes another Adirondack shelter, constructed in 2006 by Mountain . Reaching the floor of the valley, the Way joins the Military Road to reach Drumgoff Crossroads. Crossing the River Avonbeg, the route passes the remains of an old military barracks, built around 1800, and enters Drumgoff Wood. At the forest entrance is a granite pillar marking the official halfway point of the Wicklow Way. The trail follows a forest road along the flanks of Slieve Maan before briefly re-joining the Military Road and then following a forest road around Carrickashane Mountain before reaching the road at Iron Bridge where the Way crosses the Ow River. Another Adirondack shelter, again constructed by Mountain volunteers with assistance from the Glenwalk Hillwalking Club, can be found at Mucklagh, on the slopes of Carrickashane Mountain.