Participation in sporting or recreational programs can be unattainable for many disadvantaged young people. Encouraging regular cycling is an important public health strategy to increase participation in physical activity and expand personal transport options for marginalised youth. Perceptions and attitudes toward cycling were explored in eight focus groups, involving 47 young people who were experiencing or at risk of homelessness in central and south-western Sydney, Australia. The benefits of cycling for physical activity, personal transport, independence and social inclusion were recognised. Barriers to regular cycling included compliance with mandatory helmet legislation; a lack of cycling skills and experience; a paucity of cycling infrastructure and reliance on cars for personal transport; and access to affordable bicycles and equipment. A comprehensive multi-strategic approach that engages marginalised young people is required to improve access and enable increased participation in cycling activities.