CARAVAN TRIP LEADERS

Lead unforgettable group experiences out of NYC

Concrete to Countryside

We run small-to-mid size group hikes and seasonal trips (30-40 people), focusing on safety, simplicity, and community. We’re outside, year-round.

If you love the outdoors and want to help people experience that side of New York, we’d love to meet you.

MEET CARAVAN

LEARN MORE

  • We’re looking for people who:

    • Love being outside

    • Can make friends with anyone

    • Stay calm under pressure and adapt when plans change

    • Want consistent weekend work

    • Are reliable, friendly, and safety-minded

    If that sounds like you, you’ll fit right in.

  • Trip Leader: Trip Leaders are responsible for guiding our groups from start to finish.

    • Manage group pacing and safety

    • Day of coordination with the Caravan team, drivers, and vendors

    • Lead the hike

    • Run group check-ins

    • Take photos and help build the experience

    Assistant Trip Leader: Assistant Trip Leaders support the Trip Leader throughout the day. We prefer this to be an interim position until comfortable to be trip lead.

  • Trip Leaders must have:

    • CPR + First Aid or Higher Certification

    • Water Safety Certification

    Assistant Trip Leaders need:

    • CPR + First Aid or Higher Certification

    • Expected to move to Trip Leader once certifications are completed

  • Everyone begins with a Shadow hike:

    1. Apply through our survey below

    2. Interview with the Caravan team

    3. Shadow a real Caravan trip

    4. Observe how the day flows & meet the team

    5. Welcome to the Crew!

APPLY

APPLY

Interested in joining the Caravan team? Fill out a few details below — we’ll review your submission & reach out if it feels like a good fit!

WHY LEAD FOR CARAVAN?

BUILD COMMUNITY

Our trips feel like instant friend-groups. As a Trip Lead, you set the tone: welcoming, fun, and full of good energy. You’ll learn how to manage groups and become the reason someone falls in love with nature.

GET PAID TO BE OUTSIDE

If you already spend your weekends hiking, you might as well get paid for it. Caravan lets you turn your love for the outdoors into real, meaningful work

FLEXIBLE WORK

Caravan Crew is meant to fit your schedule, not overwrite it. Whether you want to lead once a month or every weekend, we’ll work around your life, not against it.