Rip's Rock from Winter Clove Inn

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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, walking, and trail running and is accessible year-round.

4.9 miles
1,046 feet

kid friendly


trail running




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.