Palenville Overlook and Sleepy Hollow Loop

HARD 16 reviews
#28 of 85 trails in

Palenville Overlook and Sleepy Hollow Loop is a 12.4 mile moderately trafficked loop trail located near Palenville, New York that features beautiful wild flowers and is rated as difficult. The trail is primarily used for hiking, nature trips, birding, and snowshoeing and is best used from April until November. Dogs are also able to use this trail but must be kept on leash.

12.4 miles
2,762 feet

dogs on leash



nature trips



wild flowers




5 months ago

The trailhead linked in the directions is bad...there's no parking, it's just the end of the road and private residences. Better to just use the Rte 23A lot, about a mile west of the country club. There's another lot off Bogart Rd. that's referenced on the trail signs in the park, but I'm not sure where on the road.

From 23A around the Harding Rd trail and Sleepy Hollow horse trail to the overlook is about 4mi, another 2mi back on the Quarry trail. The Quarry trail hugs the eastern side of the mountain and snakes down from the overlook. Don't go back to the horse trail, that just leads back north toward the campground areas. Quarry trail is dank...lots of wildlife.

Wednesday, May 31, 2017

Great hike over MDW. Tons of mud and bugs unfortunately, but bug spray and good boots helped with that. Entered from Bogart road and the trail markers didn't include the big loop that AllTrails includes after the overlook. Still a great hike though and beautiful views at the overlook.

Monday, April 24, 2017

A bit rocky in some areas, varying in incline. Took about two and a half hours to reach the picnic area (elevation is about 1,900) with frequent breaks. Didn't make it to the main outlook, but it was a delightfully tiring hike, at least for me.

Tuesday, April 18, 2017

No matter how you get here the view is amazing.
Multiple different starting points to get to this one. I started at the Harding point from the DEC lot down on route 23. Steady incline for the first couple miles, with multiple viewpoints along the way.
From the DEC lot, follow the red trail markers until you reach the sign for Palenville Overlook (1.2 miles) then follow the yellow markers.
Be sure to come back the same way otherwise you may end up at the campgrounds at North/South Lake.

Saturday, July 09, 2016

Hiked to Overlook from Scutt Rd

Saturday, June 04, 2016

My boyfriend and I started at the DEC parking lot for Harding Road Trail and followed trail signs for Palenville Overlook. The trail was tough (I should note, we are smokers, but we do hike quite a bit, and it was our first hike of the year; it took us 4h23m to the outlook and back; 9.2 mi. round trip, 2485 ft. elevation gain per my boyfriend's app) but well worth the view. It's one hell of a great workout, with a great sense of accomplishment afterward. Some nice views of the notch along the way, up, too (even better on the way down as the sun starts to go down). However, be warned of large and very protective birds of prey (golden eagles, we believe) and black bears. Came across both, on one hike the day after Memorial Day. One eagle circled us at the outlook and we had to leave. A week prior to that hike, the eagles were much more protective as their young had just hatched (we can only assume) and practically chased us off the mountain (they were following us up the hike and were above us at every break), hence why we came back a week later to finish the hike. Also, be mindful of bees (that's at least something we aren't used to on hikes, not a big deal but there were clusters of them throughout the hike). Still so worth it all. It was kind of exciting encountering all that we did. It's become a favorite trail of mine.

Monday, August 26, 2013

This trail is the reason I downloaded this app. Didn't read the trail sign correctly and went 5.8 miles down the mountain instead of to the North South Lake parking lot. If I keep this up I maybe the first athlete to accidentally get in shape for a 10 k. But I'll have to get lost a couple of 100 more times. Despite the fact this trail is labeled strenuous, if you have a lot of time and light, it's worth it. Check out the plane wreck just off the trail about one mile northwest and down hill from the over-look.

Saturday, September 02, 2017

Sunday, May 28, 2017

Saturday, October 29, 2016

Monday, September 12, 2016

recorded Kaaterskills

Saturday, May 14, 2016

Saturday, April 16, 2016

Sunday, March 27, 2016