From Tinahely‘s main square you take the R749 in a south-easterly direction to the pleasant village of Shillelagh.

After leaving the village in an easterly direction you pass through Coolboy and Tinakilly before a steady climb takes you to the lesser known and “alternative Wicklow Gap” and the welcoming Gap Pub.

From here you head northwards and cross the R747 and the Derry River close to the village of Annacurragh.

A short climb up from the village brings you to the return route westwards to Tinahely via Ballinglen.

Grade: Very Challenging

Distance: 42.2 km

Ascent: 460 m

Estimated Time: 2hrs 40mins

Town Nearest Start Point: Tinahely

GPS Start Point: 52.79976, -6.46318

Wicklow Passport Collection Points: Tinahely, Shillelagh