Dehn Craig

Trip Designer

Book a 1:1 trip planning call with Dehn for insider advice and personal recommendations and recieve a custom TripGuide following the call.

$60 for 30 min - saving hours of guesswork

Get To Know Dehn Craig

Hi, I’m Dehn—trail runner, filmmaker, father of five, and lifelong adventurer. I grew up in Lake Tahoe, where backcountry routes and alpine lakes were part of daily life. That love for wild places inspired me to launch Vacation Races, a running event series near national parks—and later, Global Adventures, where I designed multi-day travel experiences that combined endurance, cultural immersion, and unforgettable landscapes.

I’ve led ultramarathons through the desert, family backpacking trips in Yosemite, and youth groups into the wilderness to show them what they’re capable of. My goal? Help people reconnect with nature, reset their perspectives, and walk away with stories they’ll never forget. Whether you’re chasing big summits, planning your first park trip, or navigating the world with your kids in tow—I’m here to help.

Specializations

Running
Trail Running
Ultramarathoning
Families with young kids
¨Adventure isn’t just a pastime—it’s a calling. Wilderness helps us reconnect, reset, and remember what truly matters.¨

Where Dehn can help

📍 Japan

I lived in Japan for two years and completed the Shikoku Henro pilgrimage solo. I know how to travel here thoughtfully—whether you’re looking for temples, rivers, or back-alley ramen.

📍 Italy

Running and hiking through the Sentiero del Ponale above Lake Garda, sampling local citrus in Positano, and road-tripping through Rome and the Amalfi Coast—Italy is magic.

📍 California

From Yosemite to Joshua Tree, I’ve hiked, backpacked, rock climbed, and road-tripped across the state. Whether you want kid-friendly redwoods or rugged solitude—I can help.

📍 Nevada

Growing up around Lake Tahoe’s East Shore, the Flume Trail and Desolation Wilderness became my outdoor classroom. I’ve also run events and family trips throughout the state.

📍 Montana

I know both West and East Glacier well, including hidden trails and family-friendly hikes. I love Glacier for its backcountry potential and raw beauty.

📍 Wyoming

As a regular in Jackson Hole and the Tetons, I’ve guided and advised on routes for families, ultrarunners, and backpackers—including alpine lake swims and summit sunrises.

📍 Arizona

From running ultramarathons outside Zion to exploring Antelope Canyon and the Grand Canyon’s Bright Angel Trail, I’ve helped people experience Arizona’s extremes with confidence.

📍 Utah

I’ve designed events and adventures across the entire state, from Zion’s Narrows to the Parunuweap backcountry. Utah’s wild beauty has been a major chapter in my outdoor life.

📍 Hawaii

I’ve explored Big Island’s Volcanoes, Kona’s sacred sites, and O‘ahu’s hidden trails. I know how to blend culture and nature into a deep, memorable trip.

📍 France, Denmark, England

As a traveling parent, I’ve navigated Europe with five kids—blending cultural stops with downtime and outdoor escapes. I know how to make these trips smooth, educational, and actually fun.

Some happy campers

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What you get:

  • 25-min Zoom call with your expert
  • Personalized TripGuide with your recommendations, logistics info, and a day by day approach following the call
  • Custom Google map, curated by your expert

Note: your map and TripGuide are shareable so you can give to your travel companions

Send me a message

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Common Questions

How does Outdoorable work?
Outdoorable connects you with experienced outdoor pros through 1:1 video calls. Whether you’re deciding between destinations, need insider tips for a specific trail, or want advice tailored to your skill level, our experts are here to help. Simply browse expert profiles, book a call, and get the guidance you need to plan your next adventure with confidence.
What can I ask an Outdoorable expert?
Anything about your outdoor trip! Need advice on hiking routes, family-friendly trails, or navigating backcountry terrain? Want to know the best time to visit Patagonia or if a specific climb is doable for your skill level? Our experts are here to give personalized insights based on their firsthand experience.
How long are the calls?
Calls are 30 minutes, giving you plenty of time to ask questions, explore options, and get personalized advice. If you need more time, you can always book a follow-up session.
Can I choose which expert to talk to?
Yes! You can browse detailed expert profiles to find someone who matches your destination or activity needs. Whether it’s a hut-to-hut trek in the Alps or beginner-friendly kayaking in Croatia, you’ll find an expert who’s been there and done that.
What happens after I book a call?
Once you book a call, you’ll get a confirmation email with a link to share your questions or trip details in advance. This helps the expert prepare and ensures you get the most out of your session. You’ll also receive a link for the video call closer to the appointment.
How much does it cost?
A 30-minute call costs $60, with $45 going directly to the expert. We believe in fair pay for our pros who have invaluable expertise while keeping it affordable for adventurers.
What if I need to reschedule or cancel?
We get it—plans change. You can reschedule or cancel your call up to 24 hours before the scheduled time. Just head to your confirmation email for details on how to make changes.
What if I don’t find the call helpful?
We strive to connect you with the best experts and provide actionable advice. If you feel your call didn’t meet your expectations, let us know. We’ll work with you to make it right. All Pros can see your questions in advance, and they will let us know beforehand if they don’t think they are the best person to provide insight.
Can I share the call with someone else?
Yes! Whether you’re planning a trip with friends or family, feel free to include them in the call. Just make sure everyone’s ready to hop on when the session starts.
Do experts plan my trip for me or give me an itinerary?
No, Outdoorable is not a trip-planning service. Our experts provide personalized advice, answer questions, and guide you with insights to help you plan your trip. Think of it as having a knowledgeable friend with all the lowdown so you can plan your perfect trip.
How do you choose your experts?
Our experts are handpicked for their firsthand experience, regional knowledge, and ability to give actionable advice. Many are professional guides, trip designers, or seasoned adventurers with years of expertise. That means their jobs are to find the best places off the beaten path. Needless to say… you’re in good hands.
What kind of trips can Outdoorable help with?
Outdoorable is perfect for all types of nature-based adventures:
• Planning a big bucket-list adventure
• Deciding between destinations based on your outdoor skill level and interests
• Finding hidden trails, parks, routes
• Preparing for a solo trip, family outing, or group adventure