He played polo and took part in field sports including big game-hunting until in 1915 a fall from a horse left him with a curved spine and a compacted hip.
In 1925, with Colonel R. C. Wilson of the Indian Army and Howard Somervell, the Ruttledges scouted the area to the north-east of the great mountain, hoping to find an approach to it by Milam and the Timphu glacier; they eventually concluded that this would be too hazardous.
The full British complement was Frank Smythe, Eric Shipton, Jack Longland, Eugene Birnie, Percy Wyn-Harris, Edward Shebbeare, Lawrence Wager, George Wood-Johnson, Hugh Boustead, Colin Crawford, Tom Brocklebank, E. Thompson and William Maclean, with Raymond Greene as senior doctor and William 'Smidge' Smyth-Windham as chief radio operator.
The highest point attained on this attempt was 8,570 m (28,116 f), but the route was found to be too difficult and the vital camp V that should have been reached on a rare day with fair weather – 20 May – was, as a result of disagreements between team members, never established.
In 1934 Ruttledge was awarded a Royal Geographical Society Founder's Medal; his citation read 'For his journeys in the Himalayas and his leadership of the Mount Everest Expedition, 1933.'
Alongside veterans of the 1933 expedition – Frank Smythe, Eric Shipton and Percy Wyn-Harris – team members were Charles Warren, Edmund Wigram, Edwin Kempson, Peter Oliver, James Gavin, John Morris and Gordon Noel Humphreys.
Although the North Col was reached, a combination of high winds, storms and waist-deep snow made progress above 7,000 m difficult and, with the monsoon arriving early, Ruttledge called off the expedition.
This was a very big expedition, with more sahibs than there had ever been before, and a total of sixty Sherpas, which was five times as many as in 1935.In 1932 Ruttledge planned a life as a farmer and to this end bought the island of Gometra in the Inner Hebrides, just off the west coast of Mull.
Upon returning from the 1936 expedition to Everest he decided that a life at sea would be preferable, and he bought several boats – a 42-foot (13 m) converted Watson lifeboat and later a larger sailing cutter – to pursue this idea.