Forward to a friend Tweet this Share this on Facebook Share:

Home | Job Postings | Education Jobs


Hiring: Facilitators and/or Canoe Trip Guides
Organization: Trails Youth Initiatives
Location: Stouffville, Greater Toronto Area / Ontario

  • Employment type: Contract - Full-year (preference) and/or Seasonal Summer Session (Dates for each session can be found at the end of this document)
  • Contract period: October 2023 - May 2024 (1 weekend/month) and/or Summer 2024 (June 21 - August 30, 2024)
  • Remuneration: $160 - $200/day — Dependent on qualifications and experience
  • Openings available: 10+ contract positions available
  • 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 yoga.

Position Overview:

Reporting to the Program Director, Facilitators 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 (October–May) require Facilitators to be on site overnight from Friday 5pm through Sunday 5pm, 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:
    • Completed Police Check with Vulnerable Sector Screening (valid within 3 years)
    • Current Standard First Aid and CPR-C (or higher)
    • Requirement for Off-Site Summer Trip Staff:
      • Wilderness Advanced First Aid (WAFA)(or higher)
      • Bronze Cross (or higher)
        • Trails will be offering a Bronze Cross course on-site for those in need of certification on June 22-23, 2023
  • Preferred certifications:
    • Wilderness First Responder (WFR)
    • NLS
    • F-Class License
    • 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 interventions
  • Willingness and flexibility to work outside of regular business hours as needed
  • Camping and canoe tripping experience preferred

Key Accountabilities:

Leadership and Teaching

  • Reviews, prepares, and delivers Trails curriculum to participants, founded in outdoor and character education principles, and complies with the Ontario Health and Physical Education curriculum
  • Adheres to Trails behaviour management philosophy with team support, this includes positive, proactive, and constructive feedback to participants
  • Attend and contribute at regular team meetings
  • Assess learning using rubrics and other tools in an accurate and timely manner


  • Responsible for 24-hour care of participants including during program, meals, and overnight
  • Initiate first aid and crisis response as needed
  • Maintains strict confidentiality of participant information
  • Ensure site, equipment, and spaces are organized and in effective working order after use
  • Is sensitive to and able to assess emotional well-being of individuals and collective
  • Identifies and informs Director Team of issues that may affect delivery of program


  • Be respectful and professional at all times
  • Establishes and maintains healthy working relationships
  • Provides ongoing feedback and coaching to team and sets standards and expectations
  • Refer to Trails policies and procedures to answer questions and inform participants
  • Monitor email account regularly for work-related emails

Additional Duties

  • Additional duties as assigned by Director Team

Session Dates:

Weekend Session Dates:




October 13-15, 2023

November 10-12, 2023

December 1-3, 2023

January 19-21, 2024

February 23-25, 2024

April 5-7, 2024

April 26-28, 2024

October 20-22, 2023

November 17-19, 2023

December 8-10, 2023

January 26-28, 2024

March 1-3, 2024

April 12-14, 2024

May 3-5, 2024

October 27 - 29, 2023

November 24 - 26, 2023

January 12 - 14, 2024

February 9 - 11, 2024

March 22 - 24, 2024

April 19 - 21, 2024

May 10 - 12, 2024

  • Lesson preparation is an expectation of the role and must be completed a week prior to the above mentioned dates

  • A 1 hour virtual meeting with your staff team is mandatory on the Thursday prior to the weekend

Required Training:
- Sept 29 (5:30pm) - October 1 (5:30pm) - Staff training weekend
- November 4th, 2023 - 9am - 5pm
- January 6, 2024 (February 3, 2024 as a back-up date if weather is not suitable for the workshop) - 9am - 5pm

Summer 2024 Session Dates:

On site session (Stouffville, ON)

Off-site - Canoe Trip

Year 1A

July 8 - 18th, 2024

Year 5

June 25 - July 8th, 2024

Year 1B

July 22 - August 1st, 2024

Year 3

July 22 - August 1st, 2024

Year 2A

August 5 - 16th, 2024

Year 4

August 19 - 30th, 2024

Year 2B

August 19 - 30th, 2024

*Offsite trip staff require additional certifications

Required Training:
- June 21 (5:30pm) - 23 (5:30pm), 2024 - Staff Training weekend

Thank you for your interest.


Please email with your cover letter and resume and to set up an information call.

Please indicate you saw this posting at GoodWork.

To learn more, please visit our website
“ Four Seasons, For Years, For Life.”

Trails is recognized as one of Maclean’s Best Canadian Charities


Share this on Facebook   Tweet This!  Email this to a friend   Share this on LinkedIn   Add this to Google Bookmarks   Print this page

Note: The above is provided on an "As Is" basis and for general informational purposes only. People and Planet (also known as "GoodWork") is not responsible for the content, accuracy, timeliness, completeness, legality, reliability, quality or suitability of this posting. We do not screen or endorse the organizations or individuals involved. If you decide to accept an offer of employment, volunteering or any other arrangement, you do so at your own risk and it is your responsibility to take all protective measures to guard against injury, abuse, non-payment or any other loss. Please read our full Terms & Conditions.

Current status: Open/apply now.   Date posted: Aug 26 2023    ID: 67284