Facilitator - (Youth Outdoor Program)
Organization: Trails Youth Initiatives
Location: Stouffville, 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: Weekends - September 2025 - May 2026 (1 weekend/month)
Remuneration: $172.05 - $200/day — Dependent on qualifications and experience
Openings available: 2-3 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 offers an opportunity to certify at a discounted rate in the month of June
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 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
Safety
- 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
Communication
- 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
Please email opportunites@trails.ca with your cover letter and resume, and to set up an information call.
To learn more, please visit our website www.trails.ca
Trails is recognized as one of Maclean’s Best Canadian Charities
Weekends 2025/26 (You would be placed with one of the below cohorts)
FY (Y2) / IL (Y4):
- Sep 26 - 28, 2025
- Oct 31 - Nov 2, 2025
- Nov 28 - 30, 2025
- Jan 23 - 25, 2026
- Feb 27 - March 1, 2026
- March 27 - 29, 2026
- May 1 - 3, 2026
- June 6, 2026 (IL Grad)
GG (Y2) / SN (Y5):
- Oct 3 - 5, 2025
- Nov 7 - 9, 2025
- Dec 5 - 7, 2025
- Jan 30 - Feb 1, 2026
- March 6 - 8, 2026
- April 10 - 12, 2026
- May 8 - 10, 2026
- June 6, 2026 (SN Grad)
Year 1A / TCC (Y3)
- Oct 17 - 19, 2025
- Nov 14 - 16, 2025
- Jan 9 - 11, 2026
- Feb 6 - 8, 2026
- March 13 - 15, 2026
- April 17 - 19, 2026
- May 22 - 24, 2026
Year 1B / AW (Y3)
- Oct 24 - 26, 2025
- Nov 21 - 23, 2025
- Jan 16 - 18, 2026
- Feb 20 - 22, 2026
- March 20 - 22, 2026
- April 24 - 26, 2026
- May 29 - 31, 2026
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- 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 evening prior to your scheduled weekend
- Weekend hours: 5:30pm on Friday, overnight, until Sunday at 5:30pm
- Staff are paid at a daily rate x 2.5 days to account for two 24-hour periods, and expected preparation (ex. $172.05 x 2.5 = $430.13/weekend)
Required Training:
- September 19, 2025 (5:30pm) - September 21, 2025 (5:30pm) - Staff training weekend (overnight stay)
- Employees are required to attend professional development training during their contract period, with a list of approved training options to be provided by the employer no later than May 1, 2025
Job Types: Part-time, Fixed term contract
Contract length: 10 months
Pay: $172.05-$210.00 per day
Benefits:
- Casual dress
- On-site parking
Application question(s):
- Do you have experience working with vulnerable youth from at-risk, marginalized communities?
- Do you have experience working in an overnight, camp-like setting?
- Do you have a passion for working or being in the outdoors?
- It is an expectation of this role that you are able and willing to review lesson plans and be prepared prior to your weekend - is this something you can complete?
- Do you have, or are you willing to obtain the certifications required for the role, as mentioned in the job description?
Work Location: In person