Day Hike Leader

Are you someone who feels most alive in the forest, on the trail, and in community with others? Do you love sharing the magic of a crisp morning hike, a mossy overlook, or the chatter of chickadees with curious minds? If so, read on—Tripshed is looking for trail guides who can bring the land to life.

About Tripshed

At Tripshed, we believe the outdoors has the power to transform lives. Our mission is to create unforgettable outdoor adventures that foster a love for nature, inspire personal growth, and build a more sustainable world. Whether it’s the hush of a snowy ravine, a kid’s first muddy hike, or a sun-dappled walk through Carolinian forest, we’re here to make every moment count.

The Role

As a Tripshed Trail Guide, you’ll lead half-day and full-day hikes through the natural areas in and around Toronto. You’ll work with diverse groups—from young families to professionals—helping them slow down, tune in, and connect more deeply with themselves and the land.

You’ll need to be an enthusiastic leader, a steady hand, and a welcoming presence for all. Above all, you’ll create space for people to feel at home outside.

What You’ll Do

  • Lead local guided hikes in Toronto ravines, GTHA conservation areas, and forest trails

  • Share your knowledge of the land, ecology, and history with curiosity and respect

  • Help participants feel safe, welcome, and engaged outdoors

  • Manage pace and group needs with care and professionalism

  • Assist with set-up and logistics when needed (gear, snacks, etc.)

What We’re Looking For

  • Passion for the outdoors: You love being outside and helping others feel the same

  • Experience: At least 1 year of experience leading hikes or outdoor group activities

  • Skills: Friendly, confident, and great at managing group dynamics

  • Certifications:

    • Standard First Aid & CPR-C (required)

    • Wilderness First Aid (an asset)

  • Mindset: Warm, inclusive, adaptable

  • Other: Comfortable navigating Toronto-area trails; access to a vehicle is a plus

What You’ll Get

  • Pay: $100–$175 per day, depending on experience, length, and group size

  • Flexible schedule: Contract-based work, with most hikes running on weekends

  • Community: Work with a team that values the power of outdoor connection

Job Types: Part-time, Seasonal, Freelance
Contract length: Ongoing
Expected hours: 4–12 per week

To apply, please send an email to info@thetripshed.ca with "Guide Application" as the subject along with some information about yourself, a trip log, relevant experience, or a resume