Judkins decided in 1982 to organise the Coast to Coast race, and had secured sponsorship from Macpac through his friend Geoff Gabbites, one of Macpac's former directors. Judkins returned to Wanaka for the summer to organise funding for the Coast to Coast, and he organised three rock concerts; one in Wanaka and two in Queenstown. The first concert had insufficient attendance for Judkins to even break even, the second event was rained out, and it was too cold and miserable for the third concert to go ahead. Judkins sold his house to pay off his debts. The first Coast to Coast race was held in 1983 with 79 competitors. It was not until the 1986 that Judkins made his first profit from the annual event. He invested his earnings in the Ohau skifield, but it was taken out by a major avalanche on day 13 of its operation. In 1987, a television documentary was produced while Judkins held the Alpine Ironman. A lifelong fan of English singer-songwriter and guitarist Chris Rea, he took the opportunity to meet with the Brit while he was on a concert tour. The outcome of this was permission to use three titles from Rea's album "Wired to the Moon" to be used for the soundtrack. 1987 was also the year that the Coast to Coast became a one-day event.