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Rip's Rock from Winter Clove Inn is a 4.9 mile moderately trafficked loop trail located near Round Top, New York that features a great forest setting and is rated as difficult. The trail is primarily used for hiking and running and is accessible year-round.

Length 4.9 mi Elevation gain 1,046 ft Route type Loop
Hiking Running Forest Views
Description
Waypoints (30)

This round trip trail takes you to Rip's Rock, a stunning lookout of the Hudson Valley and the site where legend Rip Van Winkle slept for 20 years. Along the way the trail passes the Bareback Brook, Daisy Field, pristine forest and Indian Lookout which offers another great view. Please inform the front desk at Winter Clove Inn that you will be hiking before heading out. The trail is marked with red paint however blue paint use to be used and is still visible in some parts, hiking trails are marked with varnished wood signs while mountain bike trails have white signs. Start in the parking lot alongside the Carriage House (bowling alley) and follow the dirt and grass road towards the woods. Once entering the woods you will cross a small wood bridge and follow a trails sign directing you to the left and down a small hill towards the Bearback Brook. Cross a larger bridge and follow the trail to the left along the side of the stream. About 50 yards after the bridge look for a hiking sign pointing up a small embankment to the right. On top of this small embankment the trial will intersect with a larger trail and you will go right. The trail will then continue to tac up the hill with a few smaller mountain bike paths intersecting it, however stay on the larger trail. You will cross over a stonewall and a short distance after that you will enter the bottom of the Daisy Field. Upon entering the field you will see a trails sign pointing left, follow the trail to the left and up diagonally crossing the field. Near the upper right corner of the field the trail will re-enter the woods marked by a trails sign pointing straight ahead. Before entering the woods take a minute to turnaround and enjoy the view of the mountain range. The trail will be relatively straight and parts are covered in red shale gravel. A few minutes later you will come to a small incline with a sign pointing to the right for Websters Pass. Take this sharp right turn up a small hill and into another small clearing with a lean to on the right side. Continue straight past the lean to (after taking a rest of course) and there will be a sign for Websters Pass pointing straight ahead. Once entering the woods the ground will be covered with grass on both sides of the trial, this land used to be sheep pastures in the late 1800’s. After a short distance you will come to an intersection with Pitch Pine Path, continue straight and you will soon cross onto State Land and the trail will remain relatively flat for a little while. You will soon cross a small stream bed and in a short distance you will come to an intersection with the Lost Pond trail, continue straight on Webster’s Pass and soon you will see a stonewall on the right which runs down to another small stream bed. You will soon cross this small stream bed and in 10 -15 feet the trail will split and a sign for Websters Pass will direct you to the left and the stream will be on your left now. You will arrive at the turn-off for the Indian Lookout and Rips Rock trail on the left, bear to the left and follow the trail up a rocky hill. The trail will level out for a little before regaining its upward slope.

Weather
UV Index
Daylight
Reviews (67)
Photos (78)
Recordings (62)
Completed (93)
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Wai Che Ng
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSeptember 26, 2020
Hiking
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Erica L
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarSeptember 12, 2020
HikingWashed out

I would honestly rate this as EASY. I'm not in amazing shape and the trail is pretty boring except for the cliffs. The grade is steady and easy with just a couple steep spots here and there and they're short. There were a couple areas with some interesting geology but other than that just woods. The cliff did make it worth it though, for me. This trail isn't hard to complete but it was super annoying to navigate through the first mile. The area has SO many trails. I had to keep checking the map to read what to do at each crossing because the signs for Rip's Rock don't start until you're almost at the loop. It would be a nightmare trying to figure it out without the map. Definitely take the loop counter clockwise as intended (right at the split). The back half (after the cliffs) is slightly more interesting than the front half. And when going counter clockwise, the outlook spots get better as you move along. The view was really nice for the area. I'd say a hidden gem. I was very surprised to be completely alone. The trail itself is kind of a mess. I don't think many people hike this at all. So if you want a place to yourself, I recommend. I ran into a couple mountain bikers very early on and then nobody else, despite the inn being packed. Trail work needed. Lots of down branches and loose rocks that made it hard for me to jog. Entire first half of the loop is basically walking up an old stream, everything was loose and pitted. Back half of the trail is much nicer.

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Nick Guerin
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarSeptember 9, 2020
HikingGreat!Over grownRocky

Trail was a great hike and I would rate as moderate. The views are great although there are only two spots that have views. Trail is overgrown with brush in areas so you make want to wear pants. If you take the trail to the right at the fork the ascent is more gradual then going to the left first. Took me about 2.5 hrs.

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eric osinskie
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSeptember 6, 2020
Hiking
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Albert Covelli
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarJuly 18, 2020
BugsMuddyRocky

Great trail for beginners, with a scenic forest and very terrain, but I wouldn't call it terribly interesting. I also wouldn't rate this trail as "hard" for anyone with experience. It also had the most confusing signage I've ever seen on any trail at the start. Once you get a third of the way in you're okay and things begin to get a bit more interesting. The view is nice once you get to the top. For me, once I shifted my mind from "this will be a scenic experience" to, "this will be a decent workout", I was better off.

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Travis Lewis
Yellow StarYellow StarGray StarGray StarGray StarGray StarGray StarGray StarGray StarGray StarJuly 18, 2020
HikingBugs

The trail was fine. Not very strenuous and certainly a different style from the challenging large mountain hikes. Not sure why nobody has mentioned this...maybe we just got extremely unlucky. But there is a shooting range lass than a mile away. We heard constant gunfire the ENTIRE hike. Not a moment to relax or enjoy the wilderness. Do yourself a favor and go elsewhere. There are plenty of more enjoyable options.

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Byron Sanchong
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJuly 12, 2020
Hiking

This hike was just what my mind and spirit needed. Quiet and not flooded with noisy people or bury with cars in the parking lot. A rare gem to find nowadays. Good trail markings and amazing views

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Matt Nelson
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJuly 9, 2020
Hiking

Very rewarding, spent a few hours at the rock. Only couple on the trail. The woman at the front desk of the winter clove inn was super nice and had no problem with us parking in their lot. 5/5

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Wilson C
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarJuly 3, 2020
HikingBugsMuddy
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Natalie White
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJune 30, 2020
HikingBugs

Great trail. A little steep when you get towards the top but amazing views.

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Monica Niemi
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJune 20, 2020
HikingBugsMuddyOver grown
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Kevin Costanzo
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarJune 18, 2020
HikingBugsRocky

This particular forest is very unique in its landscape. It’s something you just have to experience. The views from Rip Van Winkles rock were stunning. There was almost no people on the trail

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Dina Signoretti-Costanzo
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJune 18, 2020
WalkingBlowdownBugsOver grownRocky

Great trail, unique diverse terrain. The views were so worth the climb. We only saw one other couple on the trail all day.

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Shay Urban
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarJune 7, 2020
HikingBugsMuddyOver grownScramble
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Gina Champion
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarJune 3, 2020
Hiking

Completed 6/3 - Trail completely empty and enjoyable hike. - Had to follow the instructions written on AllTrails to start with to find the correct path but after that it was easy to follow the markers - take bug spray - this hike is not for beginners- there are some fairly hard parts to get to the top

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Clareena Macchia
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMay 30, 2020
Hiking

Make no mistake the views at Rip Rock is extremely beautiful. This is one of my best hikes ever! Be warned that there are very steep cliffs so dangerous for kids and dogs at the top; extra care must be observed. Moderate to hard hike but bring bug spray. Also, the trail was a bit confusing at the beginning as there are many intersecting trails. Plz follow the instructions on AllTrails.

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