He branched into other areas, writing on a revolution in Portugal, flying with the RAF's Red Arrows, riding the Cresta Run, sparring with Ugandan dictator Idi Amin, and running the bulls at Pamplona. Wooldridge was newspaper columnist of the year twice, sportswriter of the year five times and sports feature writer of the year four times. His first job had been on the "New Milton Advertiser", covering the funeral of a coal merchant; he intercepted every mourner to write down his or her name – holding up the interment by more than half an hour. According to his obituary in "The Daily Telegraph", Wooldridge was sent to Alaska to cover the 1,100-mile dog sled race from Anchorage to Nome, travelling with a photographer in a one-engine aircraft steered by an old bush pilot. "You slept where you could", Wooldridge later recalled. "In trappers' huts with bare wire bedsteads to sleep on, cooking up horsemeat over a fire... We stayed with Eskimo families, Indian families – there were no hotels."