Abstract: The last 30 years has seen a re-affirmation of the importance of canoeing for Indigenous communities throughout North America. These practices put an urgency to recent re-evaluations of the role of the canoe as a national symbol. Given these changes, those who guide canoe trips professionally are working through a unique landscape. This paper examines how those guides are navigating the relationship between canoeing and colonialism. Based on semi-structured interviews with guides working in Canada, the research found that awareness of colonialism and reconciliation has impacted the practices of guides, especially around the recognition of territory the trips travelled through, the relationship with Indigenous communities, the framing of wilderness, and the learning they hoped to pass on. The paper concludes by considering how recreational backcountry travel by settler organizations can engage with current discussions of reconciliation and decolonization, specifically around the discourse of wilderness and the affirmation of Indigenous jurisdiction.