Leave Brough on the A685, passing under the A66 and keeping a weather eye out for cars coming off the sliproad.  Ride through Church Brough, pausing to admire the castle, another restored by the indefatigable Lady Anne Clifford, and St Michael’s church, of Norman foundation and extended in the 16th century.  A short stretch of dual carriageway leads to Brough Sowerby.  The Black Bull pub has several namesakes nearby, so if arranging to meet friends make sure you have the right Black Bull.  Easy undulating riding (but beware of traffic) takes you past the village of Winton and finally into Kirkby Stephen.

If you have stayed in Kirkby Stephen then head back to Brough and turn right at the clock.  Leave Brough bearing to the north on the B6276. It is 15 miles to Middleton in Teesdale and the climb up the flanks of the Pennines, which is a stiff one, begins almost at once.  Behind, there are views over the green Eden Valley almost until the road reaches and hugs the 1300ft contour. Red flags to the left of the route on the way up mark the eastern boundary of the ranges at Warcop and again the early part of the ride may be punctuated by the sound of artillery fire.  This is desolate, exposed country, with the occasional farm, causing you to appreciate the unforgiving harshness of making a living up here. After the Co. Durham border sign the road undulates until moorland gives way to greener scenery and after skirting two reservoirs, you begin the descent into Middleton in Teesdale on what has now become the B6277.  There is a sign showing both left and right into Middleton – the left option is easier.