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

New Windsor, New York Map

Overall the trail was really nice, I do however have to agree that there were some parts that were not marked clearly. I definitely do plan on coming back. Also wish that people would keep their dogs on a leash like it’s been posted and maybe watch their kids more.

Except for the poor trail markings:

Decent elevation
Good views/vantage points

I’ll go back with my hammock for an overnight

Literally the worst marked trails. Took white up and got spun around on the top and ending up heading the wrong way. Ended up in yellow which is just really jagged rocks headed down. Wouldn’t do this one again...

3 months ago

Great trail.

Hiked this trail on Sunday May 20. We went up the white trail to the top then came down the yellow trail to the dark hollow. If you go the same way then this trail is not a rated correctly. It’s rated a moderate hike but it was difficult and strenuous. You will be mostly climbing up hill and over rocks depending on your fitness level for 1 to 2 hours. The descent was not easy either. Be prepared for unsteady rocky ground, steep hills , and a few streams. We went after a week of rain so the ground was still damp, the rocks slippery, but the waterfalls were abundant and beautiful. My phone calculated the floors climbed as 102 and the mileage as 8.5. This trail was awesome and the views at the top were stunning. We did not see any other hikers the entire four hours , not a shocker when a hike is this difficult. Great for those who like endurance hikes.

4 months ago

this was a great hike with lots of different terrain. Was pretty steep going up sweet clover to jessup. make sure you pay attention at every junction. we did good until we left the megaliths. we went right instead of left, but realized pretty quick n turned around. It said megliaths were labeled but a handful of hikes here today including us didn't see the writing on stone for them either. Nice waterfalls and some nice views in several spots. I have done a lot of hikes all different ratings. I will give this hike a difficult/strenuous rating due to the continued steepness. This was a great work out hike.

It's a good hike for being so close to the city. Nice views, streams, meadows, pitch pines and rock formations. Pretty well marked but pay attention at junctions. Went up the black mark on white and came back on the yellow to the white. Met some nice folks on top who arrived from different starting points in Harriman. The trail is rocky and footing is tricky at times with small loose rocks. Good shoes and poles with serve you well, especially on the way down. Still a little muddy in spots. Waterproof shoes a good idea for now.

Beautiful trail

5 months ago

This was a nice trail. The hike up the white trail was a good climb that will get you breathing heavy. From there we followed the yellow blazes out to the megaliths for a view. A very nice man pointed out the different mountains we could see in the distance. On the return, we followed the black dot trail(white blaze with black dot). This trail was much less traveled and quiet. Overall, a nice hike

This is a great hike on either trail you take. Beautiful terrain and views.

Absolutely loved this hike in the snow, fairly easy, great views and the pitch pines were so cute!

Nice climb and OMG what a payoff at the megaliths. Windy as all hell though, super cold on the ledge even though is was not that cold that day. Maybe mid 30s.

This is one of the worst hiking trails i ever been the very beginning of the trail seem to be not well take care in few words the grass was higher than me I will considered this trail hard to moderate which I like that will give you a great workout for sure plus when you will get to the very top part of the trail is very easy to get lost because the trail is not well marked so to make sure bring a map or gps

Started/ended at Otterkill Rd TH instead. It's always a nice walk over the double ridges. Beautiful day!

Sunday, September 10, 2017

Varied terrain from lightly wooded to walking on mountain ridge. We went up white blazed (i believe the sweet clover trail) and down the yellow/teal trail (Jessup trail). For an extra treat when you get to dark hollow junction at the top take yellow/teal trail (about 15 minutes) to the Megaliths. Coming down the yellow was very rocky ankles beware. The total elevation gain including the Megaliths was over 1800 ft (says my apple watch). The total hike took us 5 hours. Following the yellow trail down along the pudding stone was difficult at times. The use of AllTrails and GPS was very helpful. If you have the whole day the hike was very rewarding with beautiful views of the entire hudson valley throughout the hike.

vast views

Tuesday, August 29, 2017

This hike will kick your ass. But it's worth every step and heavy breath you take!

Sunday, July 23, 2017

Wonderful trail, steep and more difficult than moderate in my opinion. Views at the top are gorgeous!

Thursday, July 20, 2017

Schunemunk Mtn is amazing! I took the Sweet Clover trail and it was a strenuous hike! About a mile into the hike the trail becomes very steep and rocky. I also saw two snakes on the trail. Also, the railroad tracks are ACTIVE Metro North tracks, so use caution when crossing them!

This is one of the highest peak in the Orange County ny

can't say enough about how much i love this trail. nice climb, gorgeous ledges, expansive views, varied terrain, cool megaliths, funky alpine shrubbery. i do a lot of hiking in new hampshire, and this is very reminiscent of that area- for a hike that's only an hour from NYC, this one hands-down cannot be beat. my absolute go-to hike when i'm in the area.

Thursday, June 01, 2017

Wednesday, May 24, 2017

One of my very favorites. Very run-able. Do not miss the megaliths.

Monday, April 24, 2017

Fantastic views, waterfalls, streams; this hike has it all. There are a few times when you may get off trail so keep an eye on the markers. Wear good boots for water crossings and rocky inclines.

Sunday, February 26, 2017

I would rate this a little tougher than moderate, great views, water falls, maybe there's another trail that is easier , but for the most part it was fun and different, 9.5 miles by the time we were done.

Saturday, October 15, 2016

I started on the Trestle Trail on Otterkill Rd and this was my first ever hike on a mountain. I went in excited and came back absolutely battered. The views at the top are amazing but I WARN you that if you are a out of shape beginner like me, start at an easier mountain. There were lots and lots of climbing, rock scrambling and some steep descents here as I unwittingly had to explore a lot more of the trails then I intended. Trails are marked but be aware at some intersections. You can miss a trail marking easily at some points. Definitely bring a trail map. I got lost twice and had a long grueling hike back to the car. If your a fit person this place will be an awesome adventure. Overall Schunemunk mountain is amazing and as you head further up towards the summit the views just gets better and better. Bring lots of water and be ready for a workout!

Sunday, September 25, 2016

This is a great trail. Great in both the ascent & descent. It's starts flat in the meadows but doesn't stay that way.

Monday, August 08, 2016

Fun and challenging hike.

Monday, July 11, 2016

Fun hike. Lots of wild life. I saw 2 black bear cubs, 2 deer, and lots of rattlesnakes.

Saturday, June 18, 2016

Did the 9 mile loop with western trail (Orange). The track recording failed so sorry folks. Laurels were blooming, blueberries out (ate some) and yes bear, Saw a bear. Wonderful and whimsical cairns and rock trail indicators. Loved the start and finish through the meadow and the 3 mile Ridge walk. One of the best in downstate.

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