ABSTRACT In British Malaya, Scouting promoted the virtues of the Great Outdoors and opened up space for alternative views of boyhood for indigenous boys. Although Malayan boys were no strangers to being out-of-doors prior to the movement’s introduction, Scouting established an educational framework in which outdoor learning gained traction and where the Great Outdoors came to be identified as an ideal environment for cultivating a wholesome, active, and healthy boyhood. In an era where social exchanges between colonial and colonised boys were limited, Scout activities in the open-air, notably camping and hiking, fostered homosocial bonds between boys of diverse ethnic and socio-economic backgrounds in their ‘boys-only world’. Outdoor activities also nurtured the ideal of an insouciant, yet physically demanding and vigorous boyhood, where a boy’s ‘innate gang-spirit’ and ‘tendency for mischief’ were to be encouraged. In that endeavour, the Great Outdoors was conceptualised and extoled by (adult) Scoutmasters as a desirable substitute for a boy’s very own home. By harnessing newspaper sources, Scout literature, and the oral histories of former Malayan Scouts, this paper seeks to demonstrate how Scouting shaped and regulated cultural representations and understandings of the ‘Great Outdoors’ for boys’ education during the colonial era into the post-colonial present.