Hike the Chester Challenge

Hike the Chester Challenge

My real hometown has a new hiking challenge and it is awesome!

Did you know that Pittsburgh isn’t really my hometown? It’s where I’ve lived for the past several years, but I lived most of my growing up years and graduated from high school in Chestertown, NY.


In June we stayed near Chestertown for a family vacation. It my husband’s first visit to the Adirondacks and his only request was to go hiking. So, it was an easy choice to take on the Chester Challenge with him. Believe it or not, I’d only done one of these hikes before. It’s easy to live in the Adirondacks and not appreciate what you have.

To complete the Chester Challenge, you must hike six of eight hikes outlined in the Chester Challenge brochure. Most of the trails are short at 1 to 3 miles each so you could easily complete the challenge with just three days in the area by doing two hikes in a day. Because the trails were so short we did two-a-day hikes twice because we just didn’t quite feel finished hiking after the first one.

Here’s the skinny on the six trails we completed.

Cougar Nature Trails

These trails originate behind North Warren Central School and you park in the school parking lot. The trails are well-marked and you’ll get great views of Gore Mountain ski area and the school from the top. This was the least exciting hike for me, but that might be because as a student I hiked around this area really often to the point of being kind of over it. I bet if you’ve never been before, it’s very nice.

Meade Mountain and Beckman Mountain

Summit two mountains via one trail and only hiking the full ascent of one mountain? Yes, please.


It took Kevin, my brother, and me about 90 minutes round trip to see both mountains. We arrived early in the morning while it was still cool and a little damp out. We say bright orange salamanders and a little brown frog. We only encountered one other person on the trail walking down the mountain with her dog as we were walking up.

You’ll summit Meade first, then descend slightly and re-ascent to the top of Beckman. From the Meade summit onward you’ll get excellent views of Loon Lake while you hike.

Stewart Mountain

We were on a high from hiking Meade and Beckman so we hiked Stewart Mountain immediately afterward. It’s about a ten-minute drive between the Meade/Beckman trailhead and the Stewart Mountain trailhead. The Stewart trail is less than a mile and it only took us twenty minutes to reach the summit. From there we could see Loon Lake and the summits of both Meade and Beckman. I loved getting the views from both sides of the lake in the same morning.

Chester Creek Trails


The Chester Creek Trails are mostly flat. It’s less of a hike and more of a nature walk. Small signs name the different types of trees and flowers you’ll see on the trail. An out of control fire has been turned into a learning space on the dangers of forest fires. It’s a simple loop that you access behind the Town Hall.

If you want to combine two activities in one stop, go on Wednesday for the Chestertown Farmers Market.


Kipp Mountain

Kipp was my favorite hike. It has a few steep sections, but they are short. Most of the hike is a mild to moderate incline through pines. Make sure you take your time with this one and enjoy the scenery. The view just before the actual end of the trail is the best one you’ll see here.


Palmer Pond Trail

It’s pretty insane that I’d never done this hike before. Everyone who grew up in C-town has been to Palmer Pond. How I made it through my teenage years without going out there is beyond me. Frankly, I’m bummed I never went before now. It’s gorgeous!


The hardest part of this hike is actually getting to the parking lot. Take a car that you’re okay driving over big rocks and giant holes. The road leading to it becomes dirt then becomes more of a pine needle covered trail with rocks and holes. You could park further away and walk more if you like. We’d probably have done that if we’d known about the big holes in advance.

Have you hiked the Chester Challenge? Tell me about it in the comments below!

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