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

Amazing views and a good climb

The hike is fairly easy, with a few good views. The trail itself is not very well marked. We lost our way a few times. For those without a car, the trail begins right at the train station.

My new favorite trail! Did the full thing which is close to seven miles. You see amazing view of Cold Spring, Storm King and the Hudson I believe. You also get to see some nice water sights, ruins and wild turkeys! Love this hike!

Not much of a hike. The old woods road has not been cared for in a long time. It’s overgrown and the trail markers/blazes have fallen off or been destroyed. Lots of downed trees and debris in the trail. The highlights are a nice view of the Hudson River toward Bear Mt Bridge, a small waterfall ACROSS the river, and the Garrison Institute garden. The garden is quaint but in full bloom with peonies, lavender, roses, and rhododendrons. The ruined buildings are interesting but not extensive. There is bamboo along the trail which is lovely but doesn’t make up for the poor trail condition. It’s conveniently located next to the Metro North Garrison stop, but it’s not worth a trip from NYC by itself. Maybe worth including if you do other trails in the Hudson Highlands.

I don’t know who labeled this easy, but I would list it as moderate to hard. If you go right on the blue trail, you’ll go up two steep, rocky inclines. You never have to scale or anything, but the inclines are steep for a good mile or so. The views were worth it though. The walk down is much easier. I haven’t gone all the way around, I’ve cut across the green trail, which cuts about 3 miles out. There were a few boggy patches, but the trail showed recent signs of tree cutting and such, although some areas the brush was so tight to the trails it felt like a chute.

wonderful trail around a pretty lake

Lots of ticks everywhere!

1 month ago

Great hike with an easy climb. Nice view.

2 months ago

Great hike. Good climb.

2 months ago

Perfect trail if you're searching for some solitude. Took the trout Brook connector trail to reach the Wicopee trail....hung a right eventually met up with the clove creek trail and the Wicopee ends at the junction with the School Mountain rd trail. Turned around and followed the trail back to the other end where it meets up with the Charcoal Burners trail with a nice eastern view ta boot. Saw a towhee three brown thrushes and a pair of yellow bellied sapsuckers. Very enjoyable... follow the blue blazes

5 months ago

Not a bad trail, just doesn't offer the views of surrounding hikes.

Fascinating hike with remains of old brick houses, an old monastery turned into a retreat site (garrison institute), and abandoned part of the monastery, Benedict Arnold's escape route, and amazing views of the Hudson from an historic overlook (including views of West Point). Forgot to mention the bamboo throughout the hike serving as a canopy for parts of the trail! And those old stone walls that served as property lines back in the day. All unexpected surprises!

6 months ago

I started this hike from the beginning of the Under Cliff trail in the Nelsonville Nature Preserve, saw 2 pileated woodpeckers and 2 bluebirds as soon as I stepped onto the trailhead. To access the trail from here turn on pearl st off of 301 and take it to the end, there's a parking lot and a kiosk at the trailhead. Hike was approximately 9 miles round trip this route. Followed the yellow trail to white to blue to red and back to yellow. Not many views because of the snowstorm but absolutely serene as the snow fell in the woods

It is a wonderful place for good hiking

7 months ago

Easy, scenic, and beautiful!

Pretty views of the Hudson and a great lunch spot halfway. I've done this one twice. Love the bamboo forest too.

7 months ago

Easy to get to, aerobic climbs and nice views.

8 months ago

This was an out & back photo hike.

Easy walk, nice views at the end. Not for serious hikers by any means.

trail is not well marked. we went 3.6 miles all over and could not find the waterfall. Nice views of the river amd West Point.

11 months ago

Very nice trail. But if it has better view, it would be a 5 star.

Monday, June 19, 2017

Beautiful long day. White - Blue - Red - Yellow - White. Starts out pretty difficult, mellows after Bull Hill. The elevation gain coming back is easy comparatively speaking. Encountered 3 fairly large black racers on the start of the yellow coming off red. Ruins were interesting. Views on Undercliff Yellow were stunning.

Sunday, June 11, 2017

With two kids. Decent length. Large sections of Glenclyffe Loop unmarked, particularly around civilization.

Sunday, June 04, 2017

not sure why this trail was so well rated. The "waterfall" was nowhere to be found, and the trail was overgrown with grass so badly that we had to do tick checks every 10 minutes.

Also worth mentioning is the overflow on the main path in and out. I didn't plan to walk through water on my hike, and definitely didn't appreciate the wet socks...

Tuesday, May 16, 2017

Beautiful trail

Friday, May 12, 2017

Perfect trail. Some small inclines to keep it interesting. Nice and quiet for my dog and I!

Monday, February 20, 2017

We hiked this trail on Feb 19 when it happened to be nearly 65 degrees with snow still on the ground. Beautiful hike, not strenuous even for the first hike of the season.

We had difficulty finding the chimney however and only ran into a small fire pit along the AT portion of the hike.

In winter it can be easy to lose the trail between the AT section and the loop back if following the trail clockwise. No markers for a while and the trail was flooded with melting snow.

Saturday, February 18, 2017

Chimney Trail is a very nice walk.

Thanks to Gregory & Eric's posts, we were able to discern where the trail head was, as there was only a sign for Moneyhole Mtn...

Green, to Yellow, to White was perfect guidance to follow up to the top.

Hiked it today, Feb 18th, in 50° weather. The trail was snow covered, but with good hiking boots, it was fine.
Beautiful views from the top of the snow caped mountains

Sunday, January 29, 2017

Awesome trail. To get to the "Camp fire" you want to follow the green trail to yellow to white. Its an easy trail, used it in January, if there's snow, and its begun to melt, your going to encounter a portion thats over flooded and have to go around it off trail or walk through 3" of water.

Unlike the map above this doesn't loop, but ends at the top if a hill with the chimney and a wonderful view Westward. Just follow the trails

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