Explore the most popular dogs on leash 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.

9 days ago

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

Amazing views and a good climb

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!

wonderful trail around a pretty lake

2 months 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

4 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.

5 months ago

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

7 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

8 months ago

Easy to get to, aerobic climbs and nice views.

9 months ago

This was an out & back photo hike.

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.

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...

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

Monday, December 12, 2016

I think it's more of an easy hike but very nice view from the top. The directions leave you short of the trail head. Parking is about 200 yards before the trailhead and the trailhead is across the Garrison Fish and Game Club.

Wednesday, November 02, 2016

The trail was tough in the beginning, it was hard a climb for the first mile then it leveled off and descends. There was some great views of the Hudson River and other mountains in the area. Definitely would do it again, but would try some other trails in the area instead.

Saturday, July 30, 2016

Fun camping experience for our young kids.

Monday, June 27, 2016

Absolutely beautiful vistas. Be careful to stay on the trail. Get a trail map before hiking. A little crowded at times.

Wednesday, May 25, 2016

I wasn't prepared for this long hike at all. Been reading about this trail and everyone else has been saying you can just modify it access to your style and ability. I followed the trail from Alltrails anyway. I didn't know it was freakin long. Anyway, I took the White, Blue, Red, Yellow then back to White trail. I got lost twice. Mainly because I was trying to look for the off trail scenic views. But other than that the trail markers were quite clear. be careful when the Washburn(white) and Yellow Trails meet, just keep on following the white until you see the Notch(blue) trail. What I liked about this trail is it has scenic elevations, abandoned old historic areas, brooks/streams, forest floor, and even a quarry. It isn't as busy as the Breakneck Ridge. I'd say that to me, it's just more strenuous than the Breakneck because this one is longer. Watch out for the mysterious deep well with that stone cover along the Blue trail. it was a bit creeepy. Over all, I was dead tired but I loved the fact that you feel accomplished and rewarded by the views of the trail.

Friday, April 22, 2016

Went up the blue trail. LOVED the ruins about a mile into it. We spent so much time there, the sun started to go down so we climbed a little more, but never made it to the top due to lack of time. Deff going back to climb to the top. next time going to explore the white trail.

Monday, May 25, 2015

We went up the yellow trail from the Pearl St parking lot to avoid the heavy traffic on Washburn trail. A quiet oak tree forrest was beautiful to walk through and was a good warm up for more steep sections. 3, 4 good viewpoints. You can see the entire Storm King across the river. We only saw one other couple coming down till we reached the cross section with Washburn (the White trail). Trails are well marked and well maintained (yellow trail).

Sunday, May 24, 2015

We took Appalachian Trail from 301, heading North, moderate hiking up hills and rocks. At approx 2 miles, we turned right onto Blue Trail , down rocky hill to beach and concession stand. Great workout for a day hike. Chose to return to car via 301 as we were pressed for time.

Sunday, May 24, 2015

Amazing Hike! Multiple view points and some steep parts. Definitely a good workout.

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