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Position: Canoe Trip Leader & Educator
Organization: Headwaters Wilderness Program
Location: Toronto, Killarney, Temagami, Ontario

The Headwaters Wilderness Program is a wilderness-based educational organization primarily focused on canoe trips. Our two fundamental pillars – a relationship with nature and a relationship with community – underline the work that we do. We conceive of education broadly, as the philosophy and practice of discovering how we ought to be in the world. Our aim is to develop and implement the educational philosophy and pedagogy needed in this time of accelerating disconnection and destruction of the natural world – needed for the Anthropocene. In short, we aim to practice education for the present time, aimed at the long-term.

To this end, we are looking to grow our community! Specifically, we are seeking dedicated educators to lead canoe trips on a contract basis in Killarney and Temagami this summer for teenagers and for families. However, as we are interested in relationships that take the long-view and are reciprocal, we are also looking for educators to join our team on an ongoing basis, and we hope to have contract work available year-round.

We are looking for people who fall into any (or all) of these three categories:

  • Educators interested in theorizing, developing, and practicing intentional educational philosophy and pedagogy based in a wilderness environment
  • Educators with experience and interest in leading canoe trips (for summer 2024 especially)
  • Educators interested in being part of our team long-term, either in a program leading capacity, or in regard to program development

If you would like to learn more, please read our website (particularly the “About” section) for a more detailed look at what we do:

If you’re interested and would like to apply, please contact Devin at:

For those interested in leading trips this summer, we will fill our contract positions on a rolling basis, so please get in touch as soon as possible!

Please indicate you saw this posting at

Pay: $250 per day

With kindness,

The Headwaters Team


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Current status: Open/apply now.   Date posted: May 7 2024    ID: 71117