Outdoor Leaders create the magic at Wilderness Inquiry—leading life changing outdoor experiences for people of all backgrounds and abilities!
Wilderness Inquiry’s mission is to connect people of all ages, backgrounds, and abilities to each other and the natural world through shared outdoor adventures. Inspiring personal growth, enhanced awareness of the environment, and community integration, Wilderness Inquiry adventures such as Canoemobile, Women's Trips, and Families Integrating Together encourage people to open themselves to new possibilities and opportunities—and to each other!
You don't have to be outdoorsy to work for Wilderness Inquiry! Wilderness Inquiry staff are dedicated professionals who share a common goal of making sure everyone belongs in the outdoors. As we continue to grow and learn more about what it means to make the outdoors truly inclusive, we acknowledge that representation matters. We are dedicating ourselves to continued cultural and operational improvements to make our workplace welcoming to applicants of all backgrounds, identities, and abilities.
Employment Overview + Featured Jobs
Whether you're an expert or beginner in outdoor recreation and education (or not particularly outdoorsy at all!) there is a place for you at Wilderness Inquiry. Like participants, staff come from all backgrounds, skillsets, and interests, with one thing in common: they are all passionate about making the outdoors a more diverse, equitable, inclusive, and accessible community for all. With various program trip models, staff can enjoy working on extended trips across the country or spend their days working locally and returning to their own homes every night.
Seasonal Outdoor Leader Openings Outdoor Leader seasonal positions are available from May through October (or portions within that time frame), with various staff training dates during the spring, summer and fall. A typical week for a full-time Leader consists of guiding a one or two day trip on a Monday or Tuesday, packing out and leading and extended trip Wednesday through Sunday, then resetting for the following week.
Primary Outdoor Leaders
In addition to ensuring successful, engaging, and welcoming outdoor experiences for participants, Primary Outdoor Leaders are responsible for managing and coaching teams of 1-14+ Outdoor Co-Leaders through in-person programs. Responsibilities extend beyond individual programming events to include pre-trip and post-trip support work and acting as a main liaison between Wilderness Inquiry Trip Directors, Outdoor Leader crews, and program contacts from partnering organizations. Daily life can be fun, exciting, and incredibly rewarding, but it is also a tremendous amount of responsibility that involves hard and challenging work. Primary Outdoor Leader positions are currently filled for the 2026 season. Check back for possible fall season openings.
Canoemobile Outdoor Leaders Canoemobile Outdoor Leaders are dynamic facilitators who share their excitement for exploration and learning, while building community with Wilderness Inquiry’s youth participants. Canoemobile experiences include mostly day trips within the Twin Cities Metro area as well as extended national tours ranging from 2-12 weeks in length. Lead inclusive outdoor-based field trips that incorporate canoeing, environmental education activities focused on STEM, natural resources, historical and cultural interpretation, and team-building. During the fall Canoemobile travels city-to-city with Wilderness Inquiry’s 24-foot Voyageur canoes to facilitate introductory and accessible experiences that connect youth and communities to their local waterways and green spaces. Canoemobile national tours are made up of 6-8 Outdoor Leaders and all equipment necessary to facilitate programming for an extended period of time. Canoemobile Outdoor Leader positions are currently filled for the 2026 season. Check back for possible fall season openings.
Wonder what it's like to be on a Canoemobile tour? Check out a day-in-the-life highlight of a Canoemobile leader.
Extended Trip Outdoor Leaders Extended Trip Outdoor Leaders lead multi-day trips in various destinations across the region and country including the Boundary Waters Canoe Area, Voyageurs National Park, Superior Hiking Trail, the St. Croix and Namekagon rivers, Yellowstone National Park, and more. Extended trips vary from frontcountry to backcountry settings and require a range of skill sets and experiences. Most extended trips are 3-12 days in duration. In addition to leading multi-day trips, Outdoor Leaders support the holistic delivery of Wilderness Inquiry programming and may be scheduled to lead Day Programs, Near Nature Overnight Trips, and Warehouse/Kitchen support shifts. Extended Trip Outdoor Leader positions are currently filled for the 2026 season. Check back for possible fall season openings.
Little Sand Bay Sea Kayak Outdoor Leaders Sea Kayak staff introduce the skills and pleasure of paddling and hiking in and around the beautiful Apostle Islands National Lakeshore. Typical programming is 4 days and 3 nights with some ranging up to 14 days, all beginning and ending at WI's Little Sand Bay Base Camp near Bayfield, Wisconsin. Sea Kayak Outdoor Leader positions are currently filled for the 2026 season. Check back for possible fall season openings.
Playground
Take a virtual tour of the Apostle Islands Base Camp!
With a home base in St. Paul, Minnesota, Wilderness Inquiry sits right on the bank of the Mississippi River. From this main office and warehouse location, staff are sent to countless locations across Minnesota and Wisconsin, as well as throughout the U.S., including popular National Parks such as Yellowstone and Glacier. The sea kayaking base camp in Little Sand Bay, Wisconsin takes kayakers throughout the Apostle Islands on Lake Superior's South Shore—known for its red sandstone sea caves, sandy beaches, picturesque lighthouses, and historic shipwrecks. Both locations offer lots to see and do during your off time!
If you're one of our Guides, safety is number one. We have to make sure our guests stay safe so they get that trip of a lifetime experience. Safety and customer service fall into the same boat in our minds. Guides also need to be able to deliver a lot of knowledge of the areas they are guiding in a way that keeps guests engaged. If you don't have a ton of knowledge in the areas we offer yet, don't worry, we'll set you up. We just need you to be astute at soaking the information in and being able to share it well with your passengers.
Wages
Compensation ranges from $19-$24/hour for day programs and $182-$232/day for overnights/extended tours (plus additional full day of pay for pre-trip preparation work).
Housing & Meals
Most seasonal staff are eligible for free housing in a yurt at the Little Sand Bay Basecamp in the Apostle Islands, Wisconsin. Meals on extended trips and tours are provided for all staff.
Training
Whether or not you're a wilderness expert, never camped in your life, or just interested in leading land-based local daily activities, Wilderness Inquiry will prepare you for the work you will do—including skills in leadership, risk management, camping, and disability awareness. All Outdoor Leaders, regardless of position/experience, are compensated at $19/hour and/or $182/day for training.
Professional Certification Stipends
As the cost of obtaining and maintaining certifications required for professionals in the outdoor field can be a financial burden, Wilderness Inquiry provides a $300 stipend for Leaders who work 55 trail days while holding valid certifications.
With headquarters and free staff housing located in the Twin Cities, MN, working for Wilderness Inquiry can be rewarding to the avid backcountry adventurer, the weekend glamper, the metro-based leader, or someone interested in all-of-the-above!
Community & Values
Our shared values include: We believe in seeking the exceptional — in people, adventure, work, and life. We aren’t perfect, but we push ourselves to new heights through creativity, grit, and a commitment to one another. Seeking the exceptional, we look to be better, do better, and grow into tomorrow. We are a community of individuals—by paddling together, our strengths are magnified and our weaknesses balanced. We move forward with cohesion, a shared goal, and a unified purpose. Paddling together, our load is lighter and our boat travels farther. We are people who persevere, a tenacious group in finding a way, we strive for solutions and roll up our sleeves for the work. Challenge? Accepted. We’ll use the tools we have to fashion a fix. Finding a way, an obstacle in the path becomes the next hill to climb.
Application & Connections
Join Wilderness Inquiry in 2026! If you're looking for a place to make friends, participate in cool experiences, get paid to spend time outside, and work with a crew of amazing individuals where you feel like you truly belong and make a difference, learn more about the Wilderness Inquiry community, explore all of your job options, and apply online.
