Appleby, Cumbria, Uk. 5th June, 2015. Jack Evans at the Appleby Horse Fair in Cumbria. The Fair is an annual gathering of Gypsies and Travellers which takes place on the first week in June, and has taken place since the reign of James II, who granted a Royal charter in 1685 allowing a horse fair "near to the River Eden", and is the largest gathering of its kind in Europe. Jack is undertaking a 5 week charity journey, with his Bow Wagon in Wales on his return home.