Explore the most popular trails near Pine Plains with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Pine Plains, New York Map
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Nice hard trail but not much to see except for the fire tower at the very top.

hiking
bugs
off trail
rocky
1 month ago

short but rugged hike. Well worth it once you get to fire tower. The panoramic views of the Berkshires,Catskills as well as a couple of nearby lakes are amazing!!

hiking
rocky
1 month ago

Steep and short with a great view at the top. This fire tower has some of my favorite 360 degree scenes - fields, farms, and lakes toward Pine Plains and the Catskills to your west and north. It’s a grind to climb but really short, and there’s a slightly longer detour to the top that’s easier on your legs if you’re looking for an out. Loose rocks throughout but no scrambling. Trees are close and can be buggy.

nice hike with a nice view but nothing to see unless you climb the firetower

The view from the fire tower is amazing. Definitely worth the strenuous walk up. Make sure to take the right side path at the loop split. Still a lot of uphill, but far easier than the left

hiking
blowdown
muddy
over grown
2 months ago

on Thompson Pond Trail

hiking
bugs
muddy
over grown
3 months ago

This was a very nice hike. I was pleasantly surprised by the beauty and the changing terrain. Some spots were grassy, some narrow with tree roots, other areas almost had the feel of a rainforest. It was raining on n off during our hike and it was very humid and LOTS of bugs and some wildlife. There were a few board walks and a wooden bridge that leads to some really cool cows at the end. The bridge has some areas that had fallen down and we're laying in the muck. It was still passable. I agree there are some spots of the trail that were overgrown, as well as on the bridge. Got caught by breyers several times. The cows were awesome and nice to talk to. Beautiful views of Stissing mtn. It was very peaceful and very nice views of the pond/lake.

Nice hike, but quite steep on the way up. The view from the tower is amazing and it’s a short ways up making for a nice day trip.

hiking
bugs
muddy
rocky
4 months ago

I walked up counterclockwise - short and steep. No views until you get about half way up the fire tower then bam! Amazing views out every which way. I was lucky enough to have it all to myself on a May Friday afternoon. Great place to chill for a while and enjoy the solitude. Trails up are not really marked but are very easy to follow. A little buggy, with spots of mud and lots of rocks. So the walk up and back is no picnic, but the views are well worth it.

hiking
bridge out
bugs
over grown
4 months ago

The first boardwalk through the wetlands if you go right on the white trail at the info board has a broken spot, where it sinks into the water on the right side. A 4x4 has been placed over the spot, and it’s actually very sturdy. I’m pretty hefty, over 250 pounds and it held my weight easily. I just took it slow and listened for cracks or creaking. I wouldn’t go running over it though. There’s a few spots that have gotten very overgrown, and I got snagged by thorns a few times. I did meet a friendly herd of curious cows, who joined me for part of my walk and mooed their encouragement from their side of the fence. I also met a LOT of bugs, I’m glad I brought my spray with me, cause I had to reapply twice to keep my face from being constantly attacked. But despite the bugs I really enjoyed this hike!

hiking
bugs
muddy
5 months ago

hiking
bugs
muddy
rocky
5 months ago

Went on this hike with my 8 year old daughter as one of our first moderate hikes together. We were a little unprepared, but had a wonderful time and enjoyed the challenge. A little muddy and buggy in spots, but the view from the fire tower was worth it.

Peaceful...!!!

Trail was muddy at times but in great shape. Not very well blazed, lost them a few times, but pretty well worn. Did it with 3 kids and a dog without an issue. If you stay to the right at the "Y" it's longer but not as steep. Beautiful view from the tower, definitely worth the climb!

hiking
7 months ago

I’ve hiked this trail twice now and although it’s rated as moderate, it’s a fairly serious climb. From the moment you enter the trail you continually work your way upward with very little leveling off, if you take the left fork of the loop up to the firetower, as most hikers do. Speaking of that, the Stissing tower is one of the highest in New York State, and from the top you can see the Catskill range to the west, and the Taconic range of the Berkshires to the east. Looking down, you see two small lakes and Thompson Pond, which all abut the trailhead. Once at the top of the tower be sure to look straight up. You’ll see several bullet holes in the roof of the tower!

Quick hike to the fire tower, which had beautiful views of the leaves changing! Definitely recommend wearing waterproof shoes because there are parts of the hike where you’re going through a stream or surrounding areas are muddied by the stream. Also it rained the day before we went so it was definitely more robust than usual

hiking
11 months ago

This was a nice quick hike. It took my boyfriend and I about an 90 minutes to go up and come back down and we stopped a few times to give the couple ahead of us some time. It was pretty steep but levels off in a few areas. It was a little rocky but not too bad, I did it in my sneakers. The view from the fire tower is so pretty and it’s the only view so if you don’t want to go up the fire tower I wouldn’t recommend this one.

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