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Iain Robertson embarks on a 215-mile coast-to-coast challenge of walking the Southern Upland Way, from Portpatrick on the west coast to Cockburnspath on the east coast.

In this episode, Iain heads out from Portpatrick to Castle Kennedy in the company of actor Joe McFadden. From Castle Kennedy, Iain continues as a solitary rambler, cooking himself up a storm at the Beehive Bothy. He is then is joined by Jarad Rowan, and together they soak up some of the history of the way before camping beside Loch Dee.

As the miles come and go, Iain begins to question his ability to complete the journey, but after some much-needed rest he heads towards Benbrack to camp out beneath artist Andy Goldsworthy's striking Striding Arch sculpture. However, upon being incessantly pestered by flies at the summit, he sets off in search of a better camping spot, which results in an unexpected midnight stroll.

Upon reaching Sanquhar, roughly a third of the way into his journey, Iain takes a diversion to the Crawick Multiverse. Iain is utterly charmed by Robert Jencks' installation, and enjoys his rest day while mentally preparing himself for the many miles still to come.