Program Facilitator

Job Description

Facilitator (Wilderness Guide) - Outdoor Youth 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: Summer 2026 and/or Weekends 2026/27 (1 weekend/month)

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 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)
• Bronze Cross (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

SUMMER 2026:

On site session (Stouffville, ON)

Year 1A - July 13 - July 23, 2026

Year 1B - July 27 - August 6, 2026

Year 2 (RN) - August , 2026

Year 2 (SS) - August 24 - Sept 4, 2026

Off-site Canoe Trip (Algonquin Park)

Year 5 (LIT) - June 29 - July 12, 2026

Year 3 (FY) - July 13 - July 23, 2026

Year 3 (GG) - July 27 - August 6, 2026

Year 4 (AW) - August 10 - August 21, 2026

Year 4 (TCC) - August 24 - Sept 4, 2026

WEEKENDS 2026/2027:

RN (Y2)/TCC (Y4)

Sep , 2026

Oct 30 -Nov 1, 2026

Dec 4 - 6, 2026

Jan , 2027

Feb 26-28, 2027

April 2 - 4, 2027

April 30 - May 2, 2027

Grad: June 5, 2027

SS (Y2)/AW (Y4)/IL (Y5)

Oct 2 - 4, 2026

Nov 6 - 8, 2026

Nov , 2026

Jan , 2027

March 5 - 7, 2027

April 9 - 11, 2027

May 7 - 9, 2027

Grad: June 5, 2027

1A/GG (Y3)

Oct , 2026

Nov , 2026

Jan 8 - 10, 2027

Feb 5 - 7, 2027

March , 2027

April , 2027

May , 2027

1B/FY (Y3)

Oct , 2026

Nov , 2026

Jan , 2027

Feb , 2027

March , 2027

April , 2027

May , 2027

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

To learn more, please visit our website

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

Job Types: Part-time, Fixed term contract

Contract length: 10 months

Pay: $176.00-$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