Who doesn’t like a challenge??
A difficult road.
Feel the burn.
Reap the reward!!
Sometimes that reward is intangible. It’s that feeling of victory! in the face of the near impossible, it’s bragging rights or that oh-so-satisfying “I told you so.” In outdoor adventure land, the reward is:
- The Summit. At the top you (hopefully) see a view that drops your jaw. You (hopefully) feel like you literally conquered a mountain. Because you did!
- A Patch! That sweet sweet embroidered goodness that you wear on your backpack or your cutoff jean jacket that you proudly display as a badge of honor and respect and bad-assery.
My best adventure partner, Mark, and I learned quickly the best motivation for us to get our couch-loving keisters out-of-doors is to have that tangible reward for our efforts. We will do a series of hikes that earn us patches. A patch for hiking all three mountains in this area, or twelve mountains surrounding that lake, or forty-six mountains over a certain height in a certain park.
Although we love the feeling of fresh air and the challenge of the climb, so much climb, we also like that physical reminder of our experiences. And we love using the newest hiking challenge to try out mountains we’d never heard of, or might not have climbed.
So as more and more people head outside, more and more challenges are being created for people of all ages and abilities…and more and more cutoff jean jackets are being rocked out with colored threads.
New York’s best hiking challenges:
As decided by me, Stacie, based on my mediocre hiking abilities and moderate athletic ability. Disclaimer: before starting any adventure, please do your research and find out what exactly you’re getting yourself into. We’re talking about wild spaces, folks. Always play it safe!
Chester Challenge
Location: Town of Chester
The Peaks/Trails:
- Meade Mountain
- Beckman Mountain
- Green Hill
- Catamount Mountain
- Kipp Mountain
- Steward Mountain
- Caroline H. Fish Memorial Trail
- Palmer Pond
BONUS: you only have to do six of these eleven family friendly trails! Depending on your skill level you can choose to do an easier or harder version of some of these trails. The easier trails start at .8 miles long and go up to 2.6 miles, you’ll climb mountains and walk along nature trails.
4 Moriah
Location: Lake Champlain Region
The Peaks/Trails:
- Belfry Mountain
- Big Hollow/Coot Hill
- Cheney Mountain
- Crowfoot Pond Trail
This challenge includes a mountain that gives you the most bang for you buck in the entire Northeast: Belfry Mountain. This quarter-mile walk up an old logging road feels shorter than a walk to the mailbox, and at the top you climb a tower and gaze on the Adirondack Park to the west and the Green Mountains of Vermont to the east.
This northern Adirondack challenge gives you views of the Champlain Valley that no other does.
Tupper Lake Triad
Location: Tupper Lake Region
The Peaks:
- Mount Arab
- Coney Mountain
- Goodman Mountain
These well maintained, very easy to follow trails lead to summits with outstanding views. On Mount Arab you will also find a firetower that brings you further above the treeline. The distance for each mountain is between one and two miles, one-way.
The mountains are located within 20 minutes of each other, Mark and I were able to hike all three in one day.
Fulton Chain Trifecta
Location: Old Forge Region
The Peaks:
- Bald Mountain
- Rocky Mountain
- Black Bear Mountain
Oh I loved this series of mountains with views of the Fulton Chain of Lakes. As with the Triad, this challenge also includes a firetower, on Bald Mountain. This is one of my favorite short hikes, and not just because a group of hawks swirled around the cabin of the tower while wewere in it (!!).
Saranac 6er
Location: Saranac Lake Region
The Peaks:
- Baker Mountain
- St. Regis Mountain
- Scarface Mountain
- Ampersand Mountain
- Haystack Mountain
- McKenzie Mountain
Should you do these peaks one or two at a time, this is a fairly moderate challenge, and that’s what I’d imagine most people will do.

Now let me introduce you to the concept of…The Ultra. This is when you take a challenge and hike all the mountains. In one day. Which is what Mark and I did, making a nice walk in the woods more of a death march to the finish. This was about pushing our limits doing something we love. But, the peaks were beautiful; the views, mostly awesome; the trails, some easy, some difficult.
Lake Placid 9er
Location: Lake Placid Region
The Peaks:
- Cobble Hill
- Mt. Jo
- Baxter Mountain
- Mt. Van Hoevenberg
- Big Crow Mountain
- Bear Den Mountain
- Pitchoff Mountain
- Catamount Mountain
- Hurricane Mountain
This is a lovely mix of difficulty. From the 3 mile Mount Jo overlooking Heart Lake, to the 7 mile Hurricane Mountain, with arguably the best views in the Adirondacks. Beginner hikers can enjoy this challenge, as well as advanced. The more you progress in stamina and endurance, the more hikes you do back to back in one outing. This challenge is also done as an Ultra, something on my list. However, I tend to save my marathon hiking trips for the longest day of the year.
Lake George 12ster
Location: Lake George Area
The Peaks:
- Cat Mountain
- Thomas Mountain
- Brown Mountain
- Huckleberry Mountain
- Five Mile Mountain
- Fifth Peak
- French Point Mountain
- First Peak
- Black Mountain
- Erebus Mountain
- Sleeping Beauty Mountain
- Buck Mountain
This challenge is a good introduction into the practice of combining peaks, also known as “well I’m already here…” For example: If you are planning to hike Sleeping Beauty, you will want to add Erebus to the agenda for the day as these two peaks are close together, and to do Erebus on it’s own, you’d need to hike almost to the top of Sleeping Beauty anyway. This is where hike research is very important!
This is also a great challenge to build those hiking legs. Start out on Black and work your way to the Lower Tongue Range (Fifth, French Point and First), and by the end you can call yourself a seasoned hiker!

On another note, every mountain in this challenge (with the exception of Erebus) gives you the most breathtaking views of one of the most beautiful bodies of water, The Queen of American Lakes, as Lake George is called.
Fire towers
Location: Adirondack and Catskill Parks
The Peaks: Too many to list!
For this challenge you must hike 23 of a list of 30 firetower trails; choose 18 trails of 25 in the Adirondacks, and all 5 trails in the Catskills. As with the other challenges, there is a range of difficulty levels. Starting with the .25 mile Belfry Mountain and ending on the 15.2 mile Woodhull Mountain. But don’t let that scare you. Along the way you learn so much about hiking and about yourself, and I gar-un-tee you make it the whole way.
And another thing, you’ll start to notice some mountains cross over into other challenges. Like Hurricane Mountain, this Lake Placid 9er mountain is also a fire tower! Black Mountain is a 12ster and also a tower. It’s like I always say: remember your A B Cs…Always Be Checking the internet!
Adirondack 46er
Location: High Peaks Region
The Peaks: Way too many to list!
Unless you’re from the Upstate New York region, you’re probably not familiar with this challenge. On a recent trip to the Adirondacks, it was overheard “what’s the deal with the number ’46’ anyway??” It seems completely arbitrary, but the number 46 represents the highest peaks in the Adirondacks, peaks over 4,000′. If you haven’t started hiking the 46 High Peaks, you are probably not familiar with why this challenge is such a big deal.
It’s hard. It’s remote. Unlike with the other challenges, you realize just how far you’ve gone into the wilderness, and it’s awesome.

This is the one that grabbed Mark and me. We started on Cascade Mountain (where most start) and never looked back. We finished on Mount Marcy, the tallest mountain in New York State. And now we’re looking for our next adventure.
Northeast 111
Location: Adirondacks, Catskills…and beyond!
The Peaks: HERE.
This is a lot of climbing and a lot of traveling! But if you’re in need of venturing out and away from home, try the peaks in this challenge: in addition to the 46 High Peaks and two Catskill peaks, you’ll find five mountains in the Green Mountains of Vermont on the list, 48 mountains in the White Mountains of New Hampshire, and 14 mountains in the Longfellow Mountains of Maine.
The math IS off, if you’ve been paying attention! There are actually 115 peaks.
Mark and I completed 47 of 111 (115). The rest are certainly on our list.
That’s all for now; happy hiking, friends!
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