Freelance Wilderness Guide
About Wilderness Union
Wilderness Union is Toronto’s largest outdoor adventure community, dedicated to making the wilderness more accessible to city dwellers. We run unique adventures every week, providing gear, transport, and a welcoming community of members—not clients—who often become lifelong friends.
We’re not a traditional outdoor club, and our membership reflects that. Many of our participants are young adults experiencing the outdoors for the first time, making our guides a crucial part of building a supportive, adventurous, and fun environment. Our adventures span hiking, camping, paddling, skiing, and more, all over Ontario.
You don’t need expertise in every activity, but you should be excited to lead groups through all kinds of outdoor experiences.
Why you'll love working with us
✅ Excellent pay—up to $30/hour for day trips and $250-$300/day for overnights, based on experience and qualifications.
✅ We’ll cover the cost and provide training to help you get your F (bus driver) license, making you even more valuable as a guide.
✅ Year-round guiding opportunities—steady work, even in winter.
✅ You’ll guide with a community, not clients—we focus on friendships, not transactions.
✅ Toronto-based with access to Ontario’s best adventures—every trip starts and ends in the city.
✅ A guiding job like no other. Wilderness Union is a rapidly growing startup. As a guide, you’ll have a say in how we develop and be a respected member of our team.
The Role
We’re looking for freelance wilderness guides for regular work on an ongoing basis. Most of our events happen over the weekends with occasional mid-week social events accessible by TTC. We operate throughout the year in Ontario with Toronto as our meeting point.
As a Wilderness Union guide you’ll be responsible for:
- Leading groups on one-day to multi-day backcountry adventures.
- Ensuring every trip is safe, well-organized, and fun for all participants.
- Managing gear setup, maintenance, and packing before and after trips.
- Preparing group meals on camping trips.
- Driving members to and from adventure locations in our van (if licensed).
- Assisting members with borrowed equipment (e.g., tents, snowshoes, paddles).
Who we're looking for
We hire based on personality fit first—if you’re outgoing, passionate about the outdoors, and love introducing people to adventure, we want to hear from you! We’re looking for natural community builders who thrive on connecting with people, not just leading trips.
Minimum Requirements:
✔ Wilderness First Aid certification (WFA, WAFA, or WFR preferred) or willingness to get one.
✔ Previous experience guiding or leading groups in a wilderness setting.
✔ A clean driver’s license (G-class minimum).
✔ Experience planning and leading multi-day backcountry trips.
✔ Strong hiking ability (can comfortably cover 30km in a day).
✔ Paddling experience.
✔ Familiarity with risk management strategies for backcountry trips.
✔ Eligibility to work in Canada and located in the GTA.
Bonus Qualifications (Nice-to-Have, but Not Required):
➕ F license (strongly preferred but not required—we’ll pay for it if you’re willing to get one!).
➕ Paddling and lifeguard certifications.
➕ Hike leader or other outdoor activity certifications.
➕ Experience leading winter-specific adventures (e.g., snowshoeing, backcountry skiing).
Compensation:
Day events are compensated at a rate up to $30 per hour. Overnights pay up to $300 per day dependent on experience.
How to apply:
If you’re an experienced outdoor leader who wants to guide with a growing community, earn great pay, and get paid opportunities to upskill, apply today by emailing isaac {at] wildernessunion.com with your resume.
