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 2026/27 (1 weekend/month from September - May)
Remuneration: $176 - $210/day — Dependent on qualifications and experience
Openings available: 5 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 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 Weekends:
- Completed Police Check with Vulnerable Sector Screening (valid within 3 years)
- Current Standard First Aid and CPR-C (or higher)
For Summer (On-Site):
- Completed Police Check with Vulnerable Sector Screening (valid within 3 years)
- Current Standard First Aid and CPR-C (or higher)
- Bronze Cross (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)
- 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
Other:
- 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 [email protected] with your cover letter and resume to apply for this role.
To learn more, please visit our website www.trails.ca
Proudly named one of Canada’s Top 10 Impact Youth Charities by Charity Intelligence Canada
Weekend 2026/27 Session Dates:
Cohort 1: RN (Y2) & TCC (Y4)
- Sep 25 - 27, 2026
- Oct 30 -Nov 1, 2026
- Nov 27 - 29, 2026
- Jan 22 - 24, 2027
- Feb 26-28, 2027
- April 2 - 4, 2027
- April 30 - May 2, 2027
- Grad: June 5, 2027
Cohort 2: SS (Y2) & AW (Y4) & IL (Y5)
- Oct 2 - 4, 2026
- Nov 6 - 8, 2026
- Dec 4 - 6, 2026
- Jan 29 - 31, 2027
- March 5 - 7, 2027
- April 9 - 11, 2027
- May 7 - 9, 2027
- Grad: June 5, 2027
Cohort 3: Year 1A & GG (Y3)
- Oct 16 - 18, 2026
- Nov 13 - 15, 2026
- Jan 8 - 10, 2027
- Feb 5 - 7, 2027
- March 12 - 14, 2027
- April 16 - 18, 2027
- May 14 - 16, 2027
Cohort 4: Year 1B & FY (Y3)
- Oct 23 - 25, 2026
- Nov 20 - 22, 2026
- Jan 15 - 17, 2027
- Feb 19 - 21, 2027
- March 19 - 21, 2027
- April 23 - 25, 2027
- May 28 - 30, 2027
Mandatory Training:
- Staff Prep Weekend: September 18 - 20, 2026 (Overnight stay, 5:30pm Friday - 5:30pm Sunday)
Other Information:
- Weekend hours: 5:30pm on Friday, overnight, until Sunday at 5:30pm
- Staff are paid at a daily rate x 2 days to account for two 24-hour periods, and expected preparation (ex. $176 x 2 = $352/weekend)
What to Expect: A Snapshot of a Typical Trails Weekend
Friday
5:30 PM - 8:00 PM - Weekend Preparation
8:00 PM - Participants Arrive + Light Dinner
9:00 PM - 10:00 PM - Cabin Time + Lights Out
Saturday
8:00 AM - Breakfast
9:00 AM - 10:20 AM - Program Block 1
10:40 AM - 12:00 PM - Program Block 2
12:30 PM - Lunch
1:15 PM - 2:00 PM - Rest Time
2:00 PM - 3:20 PM - Program Block 3
3:40 PM - 5:00 PM - Program Block 4
5:30 PM - Dinner
6:30 PM - 7:30 PM - Evening Program
7:30 PM - 8:30 PM - “Freebies”
9:00 PM - 10: 00 PM - Cabin Time + Lights Out
Sunday
8:00 AM - Breakfast
9:00 AM - 10:00 AM - Community Clean Up
10:00 AM - 11:00 AM - Community Meeting
11:15 AM - Lunch
12:00 PM - Participants Depart
12:00 PM - 5:30 PM - Team Debrief
Job Types: Part-time, Contract
Pay: $176.00-$210.00 per day
Application question(s):
- Do you have, or are you willing to obtain a Standard First Aid & CPR C Certification?
- Do you have, or are you willing to obtain a vulnerable sector check?
- Do you have a passion for working in the outdoors or overnight camp-like setting?
- 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 experience working with vulnerable youth from at-risk, marginalized communities?
Work Location: In person
