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Program Facilitator - Canoe Trip Guide

Job in Whitchurch-Stouffville, Markham, Ontario, Canada
Listing for: Trails Youth Initiatives
Seasonal/Temporary position
Listed on 2026-06-19
Job specializations:
  • Education / Teaching
    Youth Development, Summer Seasonal, Camp Counselor, Child Development/Support
Salary/Wage Range or Industry Benchmark: 176 - 210 CAD Daily CAD 176.00 210.00 DAY
Job Description & How to Apply Below
Location: Whitchurch-Stouffville

Employment type: Contract - Full-year (preference) and/or Seasonal Summer Session (Dates for each session can be found at the end of this document)

Remuneration: $176 - $210/day — Dependent on qualifications and experience

Applications due: Rolling hiring — please see application details at end of posting

Who Are We?

Trails Youth Initiatives is a charity and private school that provides a long-term program for vulnerable youth. We focus on fostering community, emotional intelligence, and self-knowledge through outdoor experiential education. We augment students’ traditional schooling with intentional community-building, conscious challenge, and lifelong support in order to position them for success.

Participants commit to our four-year program with a group of 20 of their peers: two weeks each summer, and one weekend per month during the school year. At this home-away-from-home camp setting, participants build resiliency by developing a connection to their peers, a connection to a place, and a connection to themselves. Trails focuses on growing and strengthening skills such as Non-violent Communication, conflict resolution, leadership, critical thinking, and reflection.

With our focus on transference, participants build positive engagement with Trails, the outdoors, and their authentic selves. Typical daily activities may include hiking, canoeing, swimming, camping, skiing, snowshoeing and mindfulness programming.

Position Overview

Reporting to the Program Director, Facilitators (Wilderness Guides) work with youth aged 11-17 in an overnight setting. Facilitators provide 24-hour supervision to participants in addition to teaching principles of healthy living and seasonal outdoor activities such as canoeing, swimming, camping skills, snowshoeing and cross-country skiing. During the summer, Facilitators are also responsible for leading camping trips at Trails Lakeside site in Stouffville (Years 1 and
2) and/or off-site canoe trips (Years 3, 4,
5) in Ontario’s backcountry (e.g. Algonquin Park, Temagami).

Weekend sessions (September–May) require Facilitators to be on site overnight from Friday 5:30pm through Sunday 5:30pm, and consist of seven sessions total (approximately one weekend per month). Summer sessions (June–August) consist of a minimum of 11 days up to 13 days consecutively, including work over weekends and holidays.

We are mindful of the value of varied experience beyond the technical requirements of a job. If your experience is close to fulfilling the criteria below, please consider applying. Trails often offers access to some courses and certifications listed below in order to equip our staff with necessary skills to be successful in this role.

Crucially, you will be passionate about the Charity’s mission to challenge and equip vulnerable youth to become contributing members of the community.

Required Skills, Qualifications, and Certifications
  • Preference is given to those who are able to commit to the full-year contract (weekend sessions and summer sessions)
  • Mandatory by first day of work :
  • For Summer (On-Site) :
  • Completed Police Check with Vulnerable Sector Screening (valid within 3 years)
  • Current Standard First Aid and CPR-C (or higher)
  • For Summer (Off-Site) Trip Staff :
  • Completed Police Check with Vulnerable Sector Screening (valid within 3 years)
  • Wilderness Advanced First Aid (WAFA or higher)
  • Trails offers an opportunity to certify at a discounted rate in the month of June
  • Completed Police Check with Vulnerable Sector Screening (valid within 3 years)
  • Current Standard First Aid and CPR-C (or higher)
  • Preferred certifications:
  • Wilderness First Responder (WFR)
  • NLS
  • Ontario College of Teachers Certification
  • Mandatory Attendance at all Staff Training (may be full-day, evenings and/or overnight)
  • Experience leading groups of youth from at-risk communities
  • Teaching and/or instructing experience
  • Strong relationship-building, interpersonal, cross-cultural awareness, time-management, and leadership skills
  • Ability to respond to shifting priorities and refocus after interruptions which may include managing challenging behaviours
  • Openness to engaging in mindfulness activities and one on one coaching with behavioural…
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