Bear Hill Preserve

By: Matthew Young
Bear Hill Preserve
Cragsmoor, NY
Bear Hill Summit: 1.5 miles roundtrip

The town of Cragsmoor is situated along the Shawangunk Ridge, only a few miles from Sam’s Point Preserve. With less than 500 residents, the town’s steep and curvy roads are quite a contrast to streets of New York City. Growing up in a small village not far from Cragsmoor, Bear Hill Preserve was always one of my favorite hiking spots. The trail itself is not particularly long or difficult, approximately 1.5 miles round trip from the parking area. It leads to the summit of  the ridge, which hosts spectacular gray and white cliffs, with a view that seems almost too good for the short mileage. Large fissures in the rock criss-cross the summit, while huge boulders rest on one another.  The slanted surface of the ridge-top makes it seem as if the boulders could roll off at any point, though they never budge.


Bear Hill can easily be hiked in addition to the Sam’s Point loop. Yet, this short trail packs a punch and can be a destination of its own. The views are slightly different than those from Sam’s Point, but what attracts me to Bear Hill the most is its lack of crowds. Bear Hill preserve has always been the lesser known little brother, but recently as more people are exploring the Hudson Valley, the amount of visitors to Bear Hill has increased. Due to this increase in visitation, there is now a $5 entrance fee. The parking lot is also relatively small, holding no more than six to eight cars at a time. Though not much of a visitor center, the small shed at the trail’s entrance does have some maps and even some Bear Hill t-shirts for sale.


The start of this hike can get muddy, especially after summer thunderstorms, but wooden planks have been placed over the muddiest sections. The trail is well established and maintained, making it easy to follow.

As you start down the path you’ll pass behind some private homes tucked away in the forest. On early autumn days, when the air is crisp and bright, you can smell the leaves and distant woodsmoke. Take a moment to enjoy the silence this hike provides as you walk among the oaks and maples.

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A few minutes down the path and you’ll come to a junction. You can either take the “Old Trail” that branches to the right, up a small rocky hill, or you can follow the “Main Trail” around the bend. I usually take the narrower “Old Trail” which winds upwards through the mountain laurel and pitch pine.

Once it levels off, you’ll notice the white birch trees which almost completely encase the trail. They form a natural archway that feels as if you are walking through a leafy tunnel. As with Sam’s Point, the trees near the ridge top are not very tall. Even the birches tend to be on the shorter side. As early as mid-August, you can begin to spot signs of fall creeping in. A few red and yellow leaves stand out from the green backdrop, while the ripe huckleberries fill the low-lying  bushes. Late Summer is a lazy time of year on the ridge. It’s somewhat nostalgic as the days shorten and a stillness falls over the area. The trees and land can sense that summer is coming to an end. 


The trail can be rocky at times, so make sure to watch your footing. The “Main trail” eventually meets up with the “Old Trail” and forms the “Cliff Trail”. Follow this towards the summit. The summit is naturally windier as you step out from the protection of the pines. The views are spectacular. With the ridge-top extending for quite some ways, there are plenty of places to sit and enjoy the scenery. The fractured rocks make perfect natural chairs. Directly ahead you can see a portion of the ridge that was burned in the most recent fires. Blackened tree trunks form a scar cutting through the tree-line.

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I like to find a comfortable spot and just soak-in my surroundings. The only sounds from the top are the faint hum of rustling leaves and a rooster’s call from a farm on the valley floor. With only a few small breaks in the canopy, the land looks carpeted in green as far as you can see. I can watch as a thunderstorm moves left to right across the valley below. The slanted stone summit can be dangerous when wet, and Bear Hill keeps the land as natural as possible, so there are no protective railings from the sheer drop of the cliff walls. The gently sloping hillsides  on the horizon seem mild and inviting compared to the walls of jagged cliffs.


In order to get from one side of the ridge to the other, some mild rock scrambling is required. You can hop from boulder to boulder and cross over some deep cracks for different views and panoramic perspectives of the mountains and valleys. Though the cave system isn’t as extensive as the Ice Caves of Sam’s Point, with a little exploring you can find some interesting and unique spots. The caves at bear hill have no direct path through them, so venturing through the rocks can be a little more perilous. 


The white stones are beautiful against a blue sky, or changing foliage, and can even blend seamlessly into the clouds on an overcast day. There is no bad time of year to experience Bear Hill, but as Autumn approaches I know I will definitely be heading up this trail a few more times.


Bear Hill Preserve has always been a place of peace for me. It has served as an escape from the crowds, and will always be one of my all-time favorite hikes for both its sentimental reasons and its sheer beauty. Though I sometimes wish this hike would remain relatively unknown, I realize that the natural beauty of Bear Hill deserves to be shared with everyone.

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