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.

hiking
3 days ago

Great hiking trail. A little rock scrambling on the way up. Stunning views especially of the Bear Mountain Bridge.

One of my favorite hiking trails. I been there 3 times this year. Easy trail with beautiful views.

hiking
1 month ago

Great view, moderate hike depending on you physical capabilities, take it slow if it's to hard.

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!

hiking
3 months ago

Great hike with an easy climb. Nice view.

hiking
3 months ago

Great hike. Good climb.

hiking
3 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

hiking
5 months ago

My family and I hiked the trail while it was snow covered. A bit challenging due to the conditions...wear good boots with aggressive tread. The view from the summit is breathtaking. Highly recommended.

hiking
6 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!

hiking
8 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

hiking
9 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.

hiking
9 months ago

Easy to get to, aerobic climbs and nice views.

hiking
10 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.

hiking
Monday, June 26, 2017

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.

hiking
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

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