I came across this hiking challenge back in 2017 and figured it would be a breeze to complete, seeing as it only consisted of 10 hikes total.
Enter life… and now 8 years have passed. I’m close… but still not quite finished with this challenge.

The challenge requires completing 4 easy-rated hikes, 3 moderate-rated hikes, 2 difficult-rated hikes, and either Snowy Mountain or Blue Mountain. Read more about the challenge requirements here.
When I originally started this challenge back in 2017, I had all the easy hikes marked off in one day. And then, when I was finally able to pick up the challenge again, I decided to start over (sort of) so that Darby could be a completer as well.
Click on the linked trails below to see the full trail reports from our hikes. (The * denotes that Darby did this hike as well.)
The EASY Hikes
- Buttermilk Falls (7/10/2017)
- Barker Pond (7/11/2017)
- Grassy Pond (7/11/2017)
- Rock Pond (7/11/2017)
- Deathbrook Falls (7/11/2017)
- Sprague Pond (9/1/2023)*
- Bullhead Pond (9/1/2023)*
- Rock Lake (9/1/2023)*
- Blue Ledge on the Hudson (8/3/2025)*
The MODERATE Hikes
- Chimney Mountain (7/27/2019)
- Castle Rock (7/23/2022)*
- Sawyer Mountain (9/1/2023)*
The DIFFICULT Hikes
- Snowy Mountain (9/13/2019)
- Blue Mountain (8/28/2021)*
I’m hopeful that Darby and I will be completers of this challenge sometime in the near future…





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