Club Benefits
I love the fact that most of the apps I use every day have been made into apps for ChatGPT and “Connectors” for Claude.
As soon as Claude implemented a bunch of recognizable Connectors, I put its Spotify integration to the ultimate test to see if its recommended playlists included better songs in comparison to ChatGPT’s usage of the same music streaming service. And to my surprise, Claude’s Spotify feature generated the type of playlists I much preferred over the ones that ChatGPT put forth.
With that first test behind me, I was excited to put ChatGPT and Claude head-to-head again — this time to see which app and connector experience actually delivers.
Article continues belowChatGPT's Picks
To find my next hiking trails in and near the New York City area, I came up with three prompts to see what ChatGPT’s AllTrails app could show me:
- “Find me 5 easy hiking trails within 90 minutes of New York with great views, under 4 miles, and minimal elevation gain.”
- “Find me 5 low-traffic hiking trails for a peaceful solo hike this weekend.”
- “If you were a local outdoor guide, what 5 trails would you insist I experience at least once this spring season?”
For the first prompt, ChatGPT’s AllTrails integration pulled up a map with 10 recommended hiking trails, each marked as a point with a detailed info card. Each listing included the trail’s name, location, user rating, difficulty level, distance (in miles) and a quick description of the route type, like out-and-back or loop.
The five standout recommendations were Mills Reservation Trail (New Jersey), Eagle Rock Red Trail Loop (New Jersey), River, Overlook and Balls Bluff Trail Loop (South Mountain Reservation, NJ), Hobble Falls and Hemlock Falls via Lenape Trail (NJ) and Staten Island Greenbelt Trail (NY).
Of those, the Mills Reservation Trail immediately stood out. ChatGPT provided a clean bullet-point breakdown of what to expect, along with a direct link to its AllTrails page, making it easy to dive deeper before heading out.
- Distance: 2.1 miles loop
- Elevation Gain: 173 ft
- Drive from NYC: ~35–45 minutes
- Why go: One of the best skyline overlooks of Manhattan without a tough climb. Quiet wooded paths with multiple scenic viewpoints.
- Best for: Relaxed afternoon walks with a rewarding view.
For the next two prompts, ChatGPT approached my request in the same manner as the first one and brought two highly-rated hiking trails to my attention that may be worth setting foot on: the Liberty Loop Trail (Wallkill National Wildlife Refuge, NY) for the second prompt and Sam’s Point and Verkeerderkill Falls Trail (NY) for the third prompt.
Claude's Picks
Claude’s AllTrails’ presentation in response to my three prompts was the same as ChatGPT in two key areas and different in another.
Just like ChatGPT, it brought up a map for each request that put 10 of the best hiking trails on display and picked out five of them as its curated picks. Those five picks each came with all the details I needed to know about it and a quick summary of why it’s worth checking out.
Here’s how Claude’s five best picks were explained in response to my first request (I ultimately chose the Battery Park City Greenway):
- High Line Park — 1.1 mi · 6 ft gain · 4.6 (star rating) — An iconic elevated rail-trail with sweeping city views. Stroller & ADA-friendly, right in Manhattan.
- Liberty State Park & New York Bay — 2.8 mi · 26 ft gain · 4.7 (star rating) — Stunning views of the Statue of Liberty and NYC skyline from NJ. Dog-friendly loop, great for wildlife spotting too.
- Battery Park City Greenway — 2.7 mi · 0 ft gain · 4.4 (star rating) — A completely flat loop along the Hudson with gorgeous harbor views. Dog & stroller friendly.
- Williamsburg Bridge Bike Path — 2.9 mi · 88 ft gain · 4.6 (star rating) — Walk across the bridge for dramatic views of the Manhattan skyline and East River. ADA accessible and stroller-friendly.
- JFK Reservoir Running Path — 1.7 mi · 39 ft gain · 4.7 (star rating) — A beloved Central Park loop with peaceful water views and the midtown skyline as a backdrop. One of the highest-rated walks in the city!
For my other two prompts, the two winning picks I decided on adding to my hiking trail playlist were the AllTrails Spring City Central Park Trail and Prospect Park Loop.
Final thoughts
After comparing ChatGPT’s AllTrails hiking trail picks to the ones Claude generated, I came away from my experiment feeling like Claude’s recommendations were better.
I liked how Claude’s picks were in a closer proximity to my home location, as opposed to some of ChatGPT’s picks being a bit further away in New Jersey and Pennsylvania. I’m a city guy at heart, so the choices Claude made me aware of and grabbed my attention since they offer gorgeous views of nature itself, lengthy distances to walk, and a beautiful city backdrop to marvel at.
ChatGPT’s picks were good, plus its added usage of AllTrails’ links to each one, the best times to go and the way it pointed out which ones it would check out (if it had legs, of course) were cool to see. In the end, however, I recognized Claude’s hiking trail choices as the ones that would benefit my personal enjoyment the most.
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