Week 42: Using AI to find a trail run

The Experiment

My daughter had a nail appointment in Diep River; an hour and a half of dead time in an area I didn't know. I'm not great at sitting still, so I thought: why not squeeze in a trail run? (I'm still behind on my 1,000km) The problem? I had no idea where to run, no local knowledge, and about 10 minutes to figure it out before we had to leave.

Could ChatGPT help me find a decent 8-10km loop in an unfamiliar suburb, quickly enough to actually be useful?

The Process

Here's how it went down:

1. The Initial Ask I started broad: "Can I trail run in Diep River, Cape Town, about 10 km?" ChatGPT came back with a feasibility check—terrain, safety, what's connected to what. It suggested an 8km loop around the Diep River wetlands and nature reserves.

2. Getting Specific I narrowed it down: "Give me the trail, starting point, loop, and GPS coordinates." It returned a structured route: start point, waypoints, rough distances, and a narrative description of where to go. No GPX file, no map; just words and coordinates.

3. Getting There The description got me to the beginning of the trail perfectly. This was the big win; in under 10 minutes, I had a viable option and clear directions to get started. No endless Googling, no rabbit holes, no wasted driving time.

4. The Run (and Where It All Fell Apart) The route description was... optimistic. It told me to run 1.2km to a certain junction. At 1.2km, I was on a boardwalk with no junction in sight. I asked two different people if they could make sense of the directions. Neither could. The distances didn't match my watch, the landmarks didn't line up, and I was officially winging it.

5. The Unexpected Wins Even though I'd lost the plot (and the route), the area was beautiful. I found myself on trails I wouldn't have discovered otherwise—wetlands, butterflies, flowers I'd never seen before.I snapped photos of the flowers and asked ChatGPT what they were. It identified them correctly (as far as I can tell).Then I spotted mushrooms. Twice. Beautiful mushrooms that looked like porcini. First one: pinkish-red cap, white gills. ChatGPT warned it could be Amanita (Not porcini and potentially lethal). Second one: brown cap, yellow spongy underside. ChatGPT flagged it as possibly Boletus satanas (Satan's Bolete), which causes severe poisoning. I did not eat Satan's Bolete. Or the Amanita. I did not die by plucking them.

The Outcome

I had a great run, discovered a beautiful area, identified flowers, avoided poisoning myself twice, and got back to the car in time to pick up my daughter.

But the route itself? Basically useless once I got past the starting point.

What Worked:

• Speed matters: Got a solid option and directions to the trailhead in under 10 minutes, which meant no wasted time researching or second-guessing

• Led me to a genuinely lovely area I wouldn't have found otherwise

• Identified plants and mushrooms in real-time

• Kept me from eating something called Satan's Bolete (and introduced me to a potentially cool name if I want to start a metal band)

What Didn't:

• The route description was impossible to follow

• Distances were wildly inaccurate

• No actual map or GPX file (despite referencing one)

• I spent more time guessing than running

Key Takeaway

AI is excellent for rapid discovery and getting you started. It helped me in finding a starting point quickly and giving a rough idea of what's possible. For time-constrained decisions, it's unbeatable. But when it comes to precise navigation? It's not there yet.

For this kind of task, I'd want a proper GPX file or a trail map, not a prose description with questionable distances. That said, I had a better adventure because I got a bit lost. Sometimes "good enough" is perfect—especially when you only have 10 minutes to plan.

Pro Tips for AI-Assisted Trail Running:

1. Use AI for speed and discovery. When you're short on time and don't know an area, it's brilliant for getting you to a viable starting point fast.

2. Don't rely on turn-by-turn directions. It's great for "here's where to go," less great for "turn left at the third tree."

3. Embrace the detour. If the route doesn't work, you might stumble onto something better.

4. Take photos and ask questions in real-time. ChatGPT's image recognition is surprisingly useful for plants and mushrooms (especially when it's stopping you from eating poison.)

5. Do not eat wild mushrooms unless you're 100% certain. And if AI tells you it might be Satan's Bolete or Amanita, definitely don't eat it.

Want to Try It Yourself?

• Ask ChatGPT (or Claude, or Perplexity) for trail suggestions in an unfamiliar area

• Get GPS coordinates for the starting point, but don't expect perfect navigation

• Use the mobile app for real-time plant/mushroom identification

• Bring a sense of adventure (and maybe a real map as backup)

• Do not eat Satan's Bolete