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Lolipop route from Winter Clove Inn, requires permission to park on and use private ground
Hiking Trail Description
This moderate hike from the Winter Clove Inn to the location of Rip Van Winkle’s 20 year slumber spot in The Catskills has so much to enjoy.
This hike was super fun, with incredible Catskills views. The overlap of deep seminal Catskills history and stunning scenery is an absurdly sweet combination. If you have a little extra time, there are many delightful side-quests along the way.
Rips Rock from Winter Clove Inn is definitely one of the best Catskills hikes.
The Legend of Rip Van Winkle
In Washington Irving’s Rip Van Winkle a shiftless, work-shy farmer, escapes his nagging wife to the Catskill Mountains where he stumbles upon several eerie figures — who turn out to be the ghosts of Henry Hudson’s crew. Participating in their game of ninepins, he drinks their liquor and falls into a 20-year sleep. Upon awakening, he finds the world vastly changed; his wife is dead, his daughter is grown, and his neighbors are strangers. Most notably, the image of King George on the inn’s sign has been replaced by one of George Washington. This change symbolizes the shift from British rule (the Tories) to American independence (the Whigs). Rip’s sleep represents the passive observer’s experience of transformative historical events. He returns to a world that has moved on without him, pointing to the inevitability and indifference of progress.
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Rip’s Rock Loop Hiking Trail
PLEASE NOTE: This hike begins and ends on private property, at the very lovely Winter Clove Inn in Round Top, New York. 95% of this route is on public lands owned by New York State but, before you begin your hike, please stop by the reception area of the Winter Clove Inn to ask permission to use their trails. The staff are very friendly and the owners are keen for respectful hikers to enjoy the trails which surround the Inn. Please make sure to carry out everything you carry in, and leave no trace.
The Rip’s Rock hiking trail includes…
- A start on private property that requires permission
- A lean-to
- Modest stream crossings
- An imposing quarry
- One of the most seminal locations in Catskills mythology
- Beautiful trails
- Crackerjack views
Allow 2½ hours for this hike.
Rip’s Rock Loop Trail Notes & Gallery
Positioned at the foot of North Mountain, the Winter Clove Inn might be the loveliest trailhead in the Catskills. Park away from the main building, past the smaller buildings on the far side.
If you’re looking at the front of the Winter Clove, this trail begins to its left, and behind where this photo was taken. So, to begin, walk away from the building and look for the dirt road and trail signage on your right.
You will be following red painted blazes most of the way. (You can ignore the older blue painted blazes.)
Deeper into the woods, you’ll find junctions which are generally well sign-posted…
But there are also many more junctions and trails in the area than either AllTrails or GaiaGPS show — so a digital navigation aid is very useful here, and will help you stay on the correct trails for this route.
Optional Side Quest 1: The Quarry
The first opportunity for a side-quest comes about 50 minutes into the hike, when you’ll see signs for The Quarry…
The Catskills are dotted with abandoned quarries, some of them really spectacular.
This imposing quarry was fun to poke around before returning to the main route.
Optional Side Quest 2: Manitou Ledge
20-25 minutes after the quarry, you’ll come to a junction from which you can leave the main route and head down to Manitou Ledge.
When you arrived at Rip Van Winkle’s slumber spot it’s immediately obvious. The ridge shown here comes down from North Mountain, so high above is North/South Lake. And the hollow now between you and North Mountain is known as Rip Van Winkle Hollow.
Rip’s Rock itself is a large flat slab with a boulder for a fine pillow.
Rip Van Winkle must have been 12 feet tall…
The view east, out toward the Hudson Valley, is stunning…
The view is so gorgeous, I didn’t notice the cute sign until my friend and I were leaving…
After Rip’s Rock
The trail continues along the top of a sheer, rugged cliff…
This area reminded me a little of the cliffs at Gertrude’s Nose.
Optional Side Quest 3: Gorge
On the return journey at 1375 feet, and before the loop closes at a junction, I heard gushing water. To my right, off-trail, was a deep gorge I’d love to explore some day. It was almost canyon-like. The trail hugs it for quite a while. It’s impressive.
Rip’s Rock from Winter Clove Inn is one of the best Catskills hikes.
These trails can also be used to access Manitou Ledge.
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The parent mountain for this hike is North Mountain.
If you do this hike, LMK how it went…
Trailhead Info for this Hike
This hike begins on private property. Pop into the reception area to ask for permission. (Staff are super friendly.)
Google Maps Location: 42.240606, -74.031291
The map below shows the exact topographic location of the trailhead
Because this route hugs the Catskill Escarpment, I had cell service for the whole of this hike. My network is Verizon. YMMV.