Instructor Spotlight: Jess Caldwell

Photo By: Ryder Redfield

Overland Expo’s network of instructors is an incredibly valuable asset when it comes to ensuring fresh, new, and exciting programming is available to our growing and diverse community year after year. After our Pacific Northwest event in 2023, long-time instructor Chef Corso recommended we reach out to Jess Caldwell, Founder of Wildkind Academy, to include her on our roster of educators. And we see why! She’s a great fit! 

Photo by Scott Turner

Not only is Jess an outdoor educator, but she is also a certified Wilderness Survival Instructor, Wilderness First Responder, and a certified health coach from the Institute of Integrative Nutrition. She enjoys foraging, hunting, archery, and nature crafting and even completed a 50-day Wilderness Immersion Course in the Mountains of Colorado at The Survival University. Jess’s classes are led by her core beliefs: “In this unique time, we are being called to live in greater communion with ourselves, humanity, and the natural world. We can awaken our senses to engage life in a more meaningful way through what I call ALIVENESS training. By becoming a student of the outdoors we give ourselves the gift of going to wild places with greater reverence and confidence. Welcome to the way of the Wildkind… for those who value joy-based living, nature connectivity, and equanimity of mind.” 

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At Overland Expo PNW, attendees will be able to find Jess teaching about survival skills, mindset, and preparedness in both the Kids Adventure Area and the Women Who Wander Pavilion. To learn more about Jess in the meantime, check out her website and read below for our Q&A.  

Overland Expo: Tell us about your rig:  

Jess Caldwell: My rig is a 2013 Toyota FJ with canvas camo seats and featuring a beautiful Wildkind green exterior paint that looks fly in the backcountry. You will see me in the mountains with a bandana around the rearview mirror and my Belgian Malinois adventure pup named Ember riding shotgun. 

Overland Expo: Where are you heading next?  

Jess Caldwell: This summer, I will be taking my rig into the mountains of Colorado near Cripple Creek at 10,000 feet. I’ll be sleeping under the stars from my hammock in the Aspen groves and enjoying lots of hiking. I will be camping for the months of July and August and finding spots that are remote! 

Photo by Jason Marsteiner

Overland Expo: What’s your go-to overlanding/camping meal?  

Jess Caldwell: A wild game like elk meat cooked in a cast iron pan with onions, garlic, salt, and potatoes. If I catch trout… that would be the ultimate dinner. 

Overland Expo: What is your best silver-lining story?  

Jess Caldwell: I went on a fishing trip on the Snake River in Idaho with a man who had one oar in his boat and only one battery for his motor. We were supposed to be out for just a few hours, so we did not have rain gear, extra water, or provisions for the night. We also didn’t have any cell service so there was no way to SOS. We got caught downriver in a massive storm and luckily found a protected spot along the cliffside rock wall to anchor. We were stuck there until about 2 am, huddled under one of the seat cushions. When the storm died down, he made a run for it with the motor barely moving us and the one oar supporting the journey. We made it back sometime in the early hours of dawn. That experience changed how I adventure. Since then, I got myself a Garmin satellite communicator, and I tell a family member my adventure plan, including my estimated return. I always pack a Go-Bag with everything I would need for at least a two-night stay in wild places, and of course, I now carry essential layers, including a rain poncho – even under sunny skies. I like to follow the #1 Rule of Survival…Don’t Die. 

Photo by Ryder Redfield

Overland Expo: What is an area of overland travel that you think you have nailed? And what is an area of overland travel that you feel you could use some improvement in? 

Jess Caldwell: As a Wilderness First Responder and Wilderness Survival Instructor, I feel comfortable in the backcountry. These skills allow me to go into wild places with more confidence. I am definitely not a mechanic however, so if something went wrong with my rig, I would be stuck living off the land until rescued! I would also like to learn how to use a chainsaw as I once found myself in a massive windstorm near the coast of Oregon and got stuck behind some downed trees. Luckily, there was a truck behind me, and the vehicle owner was able to clear our path! 

Overland Expo: Thanks for taking the time to chat with us! We can’t wait to see you at Overland Expo PNW!

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