The Chester Challenge

21st January 2021 – Updated 4 February 2021

Today it was lightly snowing and a balmy 18 degrees when we headed up to Chestertown, NY to work on the Chester Challenge. This hiking challenge is a great one for beginners and families, though probably easier to accomplish in warmer weather. Anne and I have waited to do this challenge during the winter so we can get experience hiking in the snow. Personally, I was looking forward to hiking in my new winter boots to see how they hold up in the snow. (The Oboz 7″ insulated Bridgers did not disappoint!). We were just a team of two today- Floki stayed home with his kids, needing a bit of break from the car rides. This made it easier for Anne too, as it was going to be her first time trying out snowshoes for any real distance.

Our first stop was Kipp Mountain. While it is considered a moderate hike because of some steep sections, it is still very doable. The trail had already been broken so we just wore micro spikes and used our poles on the steep parts. The trail is treed and looked so pretty outlined with the new fallen snow.

It was a relatively quick hike up to the top, which looked over Loon Lake. Being a cloudy day, our views were more of a variation of grays but still worth it.

Our second stop of the day was Stewart Mountain. This was an easy and short hike. At the beginning of the trail we came across snow covered trees that formed a tunnel, as if to direct us on to greater things at the top. The gently falling snow was so beautiful.

It is only .4 miles and a 187 ft elevation gain to the top of Stewart, but it was enough effort to keep us warmed up despite the lack of sun and low temps. Spikes and trekking poles were useful on this trail.

Next we headed over to the Palmer Pond trailhead, and for the first time ever, we were completely thwarted in our effort. There are NO PARKING signs everywhere on the narrow road leading in to the trail, which was mentioned on the challenge website, but we did not know that it wouldn’t be plowed all the way to the trailhead. Unsure of what to do (and not wanting to illegally park or trespass) Anne called the town to query about options. She had a very friendly conversation with town supervisor, Craig Leggett, who advised us to move on. With plows and school buses coming down that road throughout the day, there just isn’t any safe place to leave the car in winter. Without access to Palmer Pond, and Meade/Beckman plus Greene/Catamount also closed for the season, we would not be able to complete 6 required hikes for the winter challenge. Craig and the challenge coordinator will look into either finding an alternative hike for people to get to 6, or rewarding the winter patch for the 5 available. We will stay in contact with them and update as necessary!

We carried on to the Dynamite Hill/Caroline Fish Memorial Trails and set out on our first big snowshoe!

You can access this area from the Dynamite Hill Recreation Area or from the Caroline Fish Memorial Trailhead. We started from the Fish side, and began our trek on the perimeter trail, which is relatively flat. When we reached the sign for the Rec area trail, we decided to take a right turn to check out this foundation wall. We took the lean-to trail up to the top of the hill.

The whole trail system and summit of Dynamite Hill does not have any open views. After a short rest, we continued down the other side of the hill, meeting up with the Side Hill Trail and finishing up where we began. In total, we did 1.6 miles with 184 ft elevation gain. Not bad for a first snowshoe hike!

Up next, we went to the Chester Creek Trail, which can be found behind the Chester Central School. This is only 1 mile long and no elevation gain so we moved through it quickly. the first section of the trail leads behind the fenced sports field and meets up with this large footbridge across the creek.

The trail turns left just after the bridge and follows the creek Before looping back to the bridge. There are various informational signs and tree markers to check out along the way. We didn’t bother with our micro spikes on this short trail, but we now recommend them for people. The narrow trail along the creek edge was very icy and Anne landed on her rump.

Our final stop of the day was Cougar Hill. This trail system is located behind the North Warren Central School. Parking is available during school hours. There several trails to choose from in this area. We took the 1.3 mile Cougar Hill loop.

It is obvious that most people don’t snowshoe this trail. The post holes were a little tricky to navigate in a few spots. Overall its a simple woods walk with 200 ft elevation gain. Spikes were very helpful in the first, steeper section up the hill. Opposite the ’view’ was a beautiful cluster of birches.

Near the end of this lovely loop trail, we took a final pic to close out this great day and headed home. This challenge was perfect for our set goal. Like our ADK Snow Falls Challenge, it has been a wonderful training ground for winter equipment testing. With a few gear adjustments, we are ready to go a bit bolder!

For more information the Chester Challenge, visit https://www.townofchesterny.org/chester-challenge.html

UPDATE 2/4/21

We learned through the town clerk that the Meade/Beckman trail is indeed open during the winter season. This land is on private property and there have been times when the owner has closed access due to extreme icy conditions. The Chester Challenge web page will hopefully get updated to reflect this detail. With renewed energy, warm temps and bright sun above we strapped on our snowshoes, leashed up Floki and made the climb. There’s a 600 foot elevation gain over one mile so we definitely were feeling that awesome burn of leg muscles getting a good workout.

We reached the Meade summit in about 25 minutes and met up with other hikers- 2 women with 2 dogs and a baby. (Way to go, Ladies. Impressive!). In order to keep the dog chaos under wraps we decided to move on quickly and let them enjoy their snack time in peace. We quickly made our way over to Beckman Mountain.

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The trail from Beckman continues on in a loop, and along the way this clearing gave us a great view of the mountains north.

The loop meets back up with the main trail below the Meade summit so we had to repeat our steps on a short climb up. This summit has a rather expansive view with several peaks to see, but as an avid skier, Anne’s attention was primarily focused on the great view of Gore Mountain.

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The trail is well packed down with snowshoe tracks, so our trek back down to the car went very quickly. We drove over to the Town Clerk’s office in Chestertown in hopes of registering our completion of the challenge. The building is closed due to COVID but a phone call into the the office brought Wendy to the door with our patches in hand. We had a lovely chat with her about our experiences with the challenge and winter in the Adirondacks.

We chose to save this particular challenge for winter because we thought it would be a good starter mission for newbies on snowy trails. We are pleased to report that the Chester Challenge was perfect in every way for that purpose! We are ready for the next peak.