I Asked AI to Plan a Hike for Me. Here’s What Happened Next.

Could an AI chatbot be a weekend adventurer's new best friend?

Photo: mastaka / iStock / Getty Images Plus via Getty Images

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As an editor at Backpacker, infatuation with maps and piles of gear is in my job description. I spend my workdays (and yes, sometimes my vacation days) sweating details like trail mileage, water sources, and meal plans. But even the most organized trip planners need some help now and then. 

Earlier this summer, our team shifted to a four-day workweek. I couldn’t wait to use the extra time to go hiking; I recently moved to Washington State, where every trail seems to lead to mystical, moss-laden rainforest or glacier-capped peaks. I promised myself I’d aim to explore one new trail every week. The only problem? When you spend all week planning hikes for work, sometimes the last thing you want to do is plan one on your day off. On Friday I’d sleep a little late, and by the time I’d choose a trail, study the maps, and get out the door, the best hours of the day were already behind me. I needed an alternative to scrolling Backpacker and my handful of hiking apps. 

Like everyone on earth, I’d heard the buzz around AI chatbots like ChatGPT and Google Bard, but I was a skeptic. Until this summer, I hadn’t so much as poked around with AI. That is, until I found myself overwhelmed with trail options. 

My Virtual Hiking Assistant

I’m far from the first person to consider using AI to plan trips. Journalists at National Geographic, the New York Times, and others have written about planning entire vacations with the help of a chatbot. I read these accounts and wondered if AI could help me decide where to go hiking. 

ChatGPT or Google Bard have a slightly different approach to trip planning than a human. These tools are powered by large language models (LLMs), which consume and synthesize huge amounts of text from across the web. Using this data, LLMs excel at predicting words in a sequence. The result is a bot that can engage in human-like conversation. That makes them great at answering very specific questions. 

“Imagine you are trying to plan a trip using Google search. You cannot directly ask, ‘can you plan a trip for me in Bali?’” Wen Yang, an engineer at Outside, told me. “You will get tons and tons of ads.” Instead, you have to perform multiple searches, sort the helpful results from the unhelpful ones, and synthesize them into a plan. 

According to Yang, a chatbot can help get you to an answer more quickly by doing some of that work for you. Paired with some supplemental research, she assured me that AI tools are very effective trip-planning assistants. 

“It’s very easy talking to one tool, and you get 80 percent of the daily itinerary,” she said. 

Outdoorsy AI

I’d been toying with the idea of planning a short hike with AI when Yang and her team announced that Outside was in the process of creating its very own chatbot called Scout, which will become available to Outside+ members later this year. Scout is powered by ChatGPT, but pulls all of its information from publications in the Outside network. It doesn’t write trip reports or guides; instead, it’s kind of like having a smart friend who’s read every single article Backpacker and our sibling publications have ever written. Ask it to suggest, say, a dayhike in Yosemite or an overnight trip in the Smokies, and Scout will come back with a recommendation, plus links to well-researched, expert-written guides from Outside’s (human) journalists. Yang told me that Scout can help with trip planning, comparing gear, meal planning, and more, and that it’s designed to cater to a user’s specific interests.

I hoped that Scout might be the answer to my trip-planning woes. So on a recent day off, I decided to conduct a little experiment: I’d ask Scout where to go hiking and, as long as it was safe and legal, I’d go along with its plan.

Yang had told me that more specific questions precipitate the best results from a chatbot. So I typed in: “Can you recommend a hike in North Cascades National Park that’s between 7 and 12 miles with a view of mountains?” In response, Scout suggested two different trails and gave me some info on distance, difficulty, and the scenery. When I asked for more info, Scout also told me about a way to tack on some extra mileage, so I had even more options.

A view of North Cascades National Park from the Sahale Arm. (Photo: Ian Stotesbury Photography/Moment via Getty Images)

I decided on the Cascade Pass trail, a 7-mile out-and-back that Scout claimed had some of the most classic views of the North Cascades. 

As I continued to plan my hike, I began to run into some of AI’s limitations. Scout is built on ChatGPT, which can only access data pre-dating September of 2021. As a result, the bot couldn’t tell me anything about the current weather report, road conditions, or trail closures. However, it did suggest websites where I could find the information I needed. With a few supplemental Google searches, I had everything I needed. 

The Hike

As I drove into the Cascade Pass trailhead, I knew I was in for a good day. The views began from the road: Trickles of glacial melt streamed down steep rock walls springing from the deep green valley floor to my right. I could see snowfields and blue-tinged glaciers in the distance. And that was before I even parked. 

Once my shoes hit the dirt, things only got better. After a few shady miles through the forest, I wandered into subalpine meadows dotted with pink flowers. A dramatic ridgeline dominated the skyline on one side, with more peaks appearing as I climbed. At the pass, I gazed into a glacier-carved valley lined with some of the most attractive mountains I’ve ever seen. But I wanted more. 

Scout had told me I could continue up the Sahale Arm for even more views, and this is where the fun really began. As I climbed higher, the Cascades stretched out in every direction. I peered into a cirque at Doubtful Lake, its deep waters an enticing emerald. I strolled past six mountain goats, including three fluffy kids. On a saddle below the Sahale Glacier, I enjoyed lunch with 360 degrees of alpine vistas. I felt like I was in the Alps. Not bad for a hike a robot planned for me. 

Pleasant Surprises

As I munched on Cheetos on my drive home, I reflected on the AI-powered hiking experience. My day in the mountains was wonderful—but was it any different than a hike planned the traditional way? I’d say so.

Because I’d put so much trust into Scout before I hit the trail, my mindset on my hike was one of discovery. Normally, I’d read blog posts, look at photos, and study the maps ad nauseam, and get a good sense of my route ahead of time. This time, the whole point was to abbreviate the planning process (while still making sure I was prepared for a safe hike, of course). As a result, I was really pleasantly surprised by everything I encountered on the trail. I think that blind trust could just as easily have led to disappointment, but in this case, it was a delight.

At the same time, there were some downsides, the main one being the crowds. Unless you specify otherwise, Scout might recommend the most popular trail in an area—the Cascade Pass Trail is one of these. But despite bumping elbows with hordes of other hikers, it was a great trail to get my first taste of North Cascades National Park. Next time, I’ll ask Scout for a trail with some more solitude. And if I really want to get off the beaten path, I’ll probably plan my trip the old fashioned way—with a map. 

You can hear more about my experience hiking with AI on the Outside Podcast