Adventure Guide

OUTSIDERS; New York (NY); On-site; USD 6,000 - 12,000; Full time

Job summary

OUTSIDERS is a city-based outdoor adventure social club in NYC seeking Adventure Guides to lead public, private, and corporate adventures. You will ensure a safe, organized, and fun experience and help newcomers feel welcome while maintaining group morale.

You’ll handle day-of logistics, greet participants, verify waivers, and coordinate with the operations team. You’ll make real-time decisions on pace, weather, and trail conditions, following safety protocols and keeping everyone engaged.

Qualifications

• Real outdoor experience with hiking on moderate to strenuous trails in NY/NJ area.
• Comfortable with scheduling and team communication tools.
• Available on weekends (Saturdays and Sundays) and some weekday evenings.
• Based in or near NYC.

Responsibilities

• Lead assigned public, private, and corporate adventures from meetup to wrap.
• Arrive early, brief with the operations team, and review the run of show (ROS) before each event.
• Greet and check in participants, confirm waivers, and set an inclusive, upbeat tone.
• Manage pace and group flow on the trail, keep the group together, and make real-time calls on weather, trail conditions, and timing.
• Follow OUTSIDERS safety and liability protocols, including emergency procedures.
• Stay in contact with the operations team before, during, and after events (guide group chats and Friday guide calls).
• Help with logistics: transportation and van coordination, setup and teardown, and partner product and snack distribution.
• Support photographers and videographers with content during the event.
• Represent OUTSIDERS and our partner brands well.
• Submit a short recap after each event: incidents, participant notes, and ideas to improve.

Skills

Outdoor experience

People orientation

Safety judgment

Reliability & punctuality

Communication

Weekend availability

Digital tools usage

Job description

OUTSIDERS is a city-based outdoor adventure social club. Our tagline: Nature Is The New Nightclub.

Founded in 2017, we are celebrating our 10-year anniversary.

Chapters in New York, Stockholm, Chicago, and Los Angeles.

We build community through shared outdoor experiences: hikes, camping weekends, kayaking, foraging, farm visits, snowtubing, and destination trips.

Our goal is affordable, accessible adventures, so more people can connect with nature and with like-minded people.

Our members are urban explorers, music lovers, outdoor enthusiasts, creatives, and food lovers.

We also design custom corporate and private outings in NYC, tailoring the activities, catering, and add-ons for each group.

The Role

Adventure Guides are the on-the-ground leaders and the face of OUTSIDERS during group adventures, hikes, and community experiences.

You are responsible for a safe, organized, fun experience for every participant.

You lead the day-of logistics and keep group morale up.

You make every participant feel welcome and part of the community, especially first-timers and people who came alone.

What You'll Do

Lead assigned public, private, and corporate adventures from meetup to wrap.

Arrive early, brief with the operations team, and review the run of show (ROS) before each event.

Greet and check in participants, confirm waivers, and set an inclusive, upbeat tone.

Manage pace and group flow on the trail, keep the group together, and make real-time calls on weather, trail conditions, and timing.

Follow OUTSIDERS safety and liability protocols, including emergency procedures.

Stay in contact with the operations team before, during, and after events (guide group chats and Friday guide calls).

Help with logistics: transportation and van coordination, setup and teardown, and partner product and snack distribution.

Support photographers and videographers with content during the event.

Represent OUTSIDERS and our partner brands well.

Submit a short recap after each event: incidents, participant notes, and ideas to improve.

What We're Looking For

Real outdoor experience: you are comfortable hiking moderate to strenuous trails and leading groups in the Hudson Valley, Catskills, and NY/NJ area.

You are a people person who can get a group of strangers talking and make solo attendees feel at home.

Calm, sound judgment under pressure. Safety comes first.

Reliable and punctual: you show up early and follow through.

A clear communicator with both participants and the team.

Available on weekends (most adventures are Saturdays and Sundays) and some weekday evenings.

Based in or near NYC.

Comfortable with digital tools for scheduling and team communication.

Nice to Have

Wilderness First Aid, Wilderness First Responder (WFR), or Wilderness EMT certification, and CPR.

NYS DEC Licensed Guide, or willingness to get licensed (we can help with the process).

Experience guiding, teaching outdoor skills, hospitality, or event production.

Specialty skills like climbing, kayaking, foraging etc

Knowledge of local trails and parks.

The Details

Independent contractor role, paid a flat rate per event depending on event type and length.

Referral bonuses for corporate, private, or group bookings you bring in.

Flexible: pick up the events that fit your schedule.

Growth: help pilot new adventures and mentor new guides.