One year later, after twelve months of extensive planning, regrouping and obtaining some of the best endurance horses in South Africa, Barry and Joe are back to undertake Sir Harry Smith's ride; determined to chase him all the way to Grahamstown. As day one kicks into gear, Barry and Joe set of on a daunting 166 km ride. During Smith's time, the old wagon road travelled through the sandy dunes of the Cape Flats but, nearly two centuries on, the brothers-in-law have to battle in the dark through a highly urbanized modern landscape. As the first light creeps in, the modern riders are neck and neck with Harry Smith, ascending the monstrous Hottentots Holland Mountains, which since colonial times have been known as the "Gateway to Africa". Second time around Barry and Joe conquer it without a hitch and set off, to their end of day destination, close on the heels of the historic hero. They've managed to perform brilliantly on their first day back on The Ride, but the question remains whether they are truly prepared for the grueling 784km that still lie ahead.