The mid-August morning was cold and crisp, with a bluebird sky. The weather was perfect for a hike in the Lake George Area. The day’s hike would be a new notch in my hiking belt. I was headed for Kipp Mountain, a 1.92 mile out-and-back trail in Chestertown that is one of the Chester Challenge hikes.

Kipp Mountain is the second Chester Challenge trail I’ve hiked. The Chester Challenge is a hiking challenge based in Chestertown. Hikers must visit six of the eight locations to complete the Chester Challenge and receive their pin. Most of the hikes are short and rated as easy or moderate. Some are simple walking trails.

I left Bolton Landing and drove north on I-87 for one exit. I took a left off of Exit 25 and drove south on Route 8 towards the town of Chester. A right on Landon Hill Road and a left on Ben Culver Road brought me to a deserted dirt parking lot and the trail head for Kipp Mountain. The lot was empty with room for about 10 cars. The road was silent.

Kipp Mountain Trail Markers

I was flying solo today, so I sent off a text to my girlfriend to let her know I was hiking Kipp Mountain. Better safe than sorry! I grabbed my back pack and and walked over to the trail register. There wasn’t a cloud in the sky and the morning’s cold was still burning off. I opened the box to find a soggy and ink smeared notebook. Recent rain had dampened the dozens of signatures in the notebook. I signed my name, noted the time and date, and closed the box. I hit the trail at 8:50 a.m.

Kipp Mountain is a 1.92 mile round trip hike. The peak elevation is 1,612 feet, with an ascent of 672 feet. The sign posted at the trailhead estimates that the hike takes about two hours. The trail heads east after the trailhead for an extended flat section. The trail is narrow and made up of dirt and pine needles, with a maximum width of about three feet. The protruding boulders that are common on other trails, like the Schumann Preserve at Pilot Knob, aren’t there to trip you up on Kipp Mountain.

Yellow Kipp Mountain trail markers help hikers head in the right direction. The trail is distinct and easy to follow and the trail markers are common. Yellow arrows posted on trees literally point towards the trail. Like most Lake George Area hikes, you’re not going to get lost on Kipp Mountain. Follow the signs, stay on trail, and you’ll be fine.

The trail travels east for an extended flat section and then pulls a gradual U-turn before heading west. Up to this point the hike is only a walk in the woods. The trail briefly climbs,  then drops back down, but there are no real increases in difficulty.

I could hear birds chirping and flying from tree to tree, but that was about it. As I’d noted earlier, this trail begins on a quiet road in a small town, so even the commonly heard rush of a car driving by is rare.

I love hiking tight and narrow trails like this. It’s a single file, three foot path that winds through a serene forest. The surrounding forest is wide open in some areas and clustered in others. Fallen dead trees litter the boundaries of the trail. The trees above me were full and green. Vast fields of ferns follow both sides of the trail and the sun broke through just enough to illuminate the forest.


Kipp Mountain is a trickster. I thought that the real climb was about to start when I hit a “Do Not Enter” sign that was blocking off what looked like an old road. It was a false start. What looked like the beginning of an incline was only another stretch of flat path. “Do Not Enter” and “Respect Landowner Property” signs are common on Kipp Mountain. Respecting these signs goes a long way towards trails staying open to the public in the Lake George Area. Many trails border privately owned land.

The next false start cam when I stopped to read a sign posted on a tree. The “You Are Here” sign showed me where I was and where I was going. I was currently in the middle of the U-turn the trail takes. Ahead of me was a widening trail and the beginning of a definite incline. I took a deep breath and trudged towards the climb.

The path had widened to about six feet in some spots, and the grade of the trail was increasing. Still, this hike was still rating out as easy. I strolled even farther, loving how alone in the woods I was. There were young swathes of trees and rambling fields of grass on the sides of the trail. Sun continued to poke through the canopy of the trees and the morning cold was beginning to burn off.

Trail Marker

Kipp Mountain

Suddenly, the climb began. The trail narrowed again, winding left and right, with a few rocks to dodge on the trail. The trail resembled a steep and serpentine herd path that made me feel like Frodo and Samwise trekking through Mordor. I didn’t spot any orcs, though I did find some scat that I couldn’t identify even after a Googling spree.

According to the Chester Challenge website, there’s an “official tree farm” on the Kipp Mountain property. I’m not sure what a tree farm looks like, but I assume I crossed through it at some point.

The trail continues to twist and turn, with roots and rocks now popping out of the trail to grab your boots. Grass fields line both sides of the trail. Up ahead is that tell-tale sign of a view – bright blue sky between the trees.

Ridge to the Left

Eventually, the trail starts to follow a ridge on the left. Don’t stray too far towards your left. The ridge drops off fast and steep. Loon Lake looms below in all of her glory. The small lake looks remote and peaceful on this August morning.

The ridge line travels with the trail for the rest of the hike. There are several places to stop and check out slightly different views. What looks like a tent platform sits just off the trail waiting for a hungry hiker to sit for a sandwich. I didn’t bring any food but I did squat down for some water.

Gore Mountain, with its currently snow-less trails, rises in the west. Meade Mountain and Beckman Mountain, two other Chester Challenge hikes, can be seen as well. Prospect Mountain and Crane Mountain pop up towards the southwest. The view is a bit overgrown in some spots. There aren’t many unobstructed glimpses, such as what you can find at The Pinnacle. I’m sure the view is awesome in fall and winter. You’ll know when the trail ends because, well, there’s a big yellow “Trail Ends Here” sign. You can’t miss it.

Trail Ends Here

I walked around at the summit for a while, chugged some water, took some photos, and then started my climb down. As usual, the walk down went faster than the hike up. Other than the brief steep section, the stroll down was another wonderful walk in the woods. I arrived back at the trail register at 10:15 a.m., but that was because I sat around at the top, then stopped to take pictures of mushrooms, weird rocks, and four trees that flared out of one trunk. Were I not taking dozens of pictures I think I could’ve hiked out and back much faster. Then, I headed to The Crossroads for a bacon, egg, and cheese. A hiking tradition.

Overall, Kipp Mountain is an awesome member of the Chester Challenge. It’s another example of a short hike with rewarding views. I rate it as easy-moderate. Most of the trail is just a casual walk through the woods. The steep part will be challenging for some people, but it’s a short challenge. If you’re in decent shape you’ll probably find that Kipp Mountain leans more easy than moderate. As usual, the BEC sandwich was an obvious ten.