Gurdial Singh joined The Doon School in 1945 and it was here that he was influenced by Englishmen such as John Martyn, R.L. Holdsworth and Jack Gibson to take up mountaineering. The first headmaster of Doon Arthur Foot was a member of the Alpine Club. Together, they scaled many peaks including Bandarpunch, Trisul, Kamet, Abi Gamin and Nanda Devi. He was the first Indian member of the famed Alpine Club, which was a club of English gentlemen devoted to mountaineering. In 1965, Singh climbed Mount Everest as a member of the first successful Indian expedition, led by Mohan Singh Kohli.