Background you can feel free to skip: If there’s a cooler short hike in the Hudson Valley than Bear Hill Preserve, I’m not immediately calling it to mind.
This hike is perfect for a family outing, assuming you have a relatively high tolerance for watching your kids climb around on huge rocks, and you trust them not to fall off cliffs, and your wife is not there to question your judgement.
My wife, Kara, didn’t accompany us for this trip – instead, my buddy Sergey and I combined our offspring (three boys) and went on a big fat bro outing (five bros total). It turned out to be the perfect adventure for that day, but I can see how it wouldn’t be for everyone with small kids. This is not the place to bring a person, little or otherwise, who doesn’t respect gravity.
“You would have had, like, seventeen heart attacks if you’d seen what we did there,” my six-year-old son reported to Kara upon our return home.
“Somebody died there,” my three-year-old son chirped in. I didn’t realize he’d heard the park steward tell me that. Apparently, some years ago, at least one person did fall off the cliffs and die.
Kara looked at me.
“Dude, we were perfectly safe the whole time,” I said, while my mind wandered to which photos from the day I needed to delete.
Try Googling “Bear Hill Preserve” and you won’t turn up too much information on this place, aside from some cool photos dotting the Internet. We couldn’t even find decent directions or an address, and ended up exploring some dirt-road dead-ends before finally locating the preserve (and thank you to this botany site for giving us enough information to crack the case, as we drove around and tried not to swear in front of the kids).
One of the great things about this hike is that it illustrated to me, yet again, that you can actively seek out great places to hike around here for more than a decade, and still find great new places to explore.
This place is high on my list of awesome Hudson Valley locations, and it’s fun to keep that list growing. If you decide to pay a visit, I can almost guarantee it’ll expand your list, too.
1. From the parking area (see “Directions to the trailhead” below), head over to the wooden booth and settle your debts (see the “Cheapskate alert” above). On the day we visited, a sweet woman named Corinne greeted us, chatted us up, and offered us bug spray. The kids and grown-ups were all in agreement: Corinne is super cool.
I also wasn’t really expecting a human to be inside that booth, and I kind of jumped a little when I saw her through the camera. So, you know, be ready for a human in there. A very cool human.
2. Time to get crackin! Just to the right of the wooden booth, follow the well-trodden trail around the Bear Hill Nature Preserve sign and the bronze plaque that both mark the trailhead. (There aren’t any trail markers here, but the trail is obvious enough that you won’t need any.)
3. Hey, a boardwalk! You can’t get cheese fries or tacky T-shirts here, but it’s still a nice place to stroll. Also, TOAD!!! Toad! There’s a toad down there, everybody. Stay cool. Toad.
4. From the boardwalk, just follow the trail, which alternates between having a deep-woods vibe and feeling like you’re walking through someone’s backyard.
If you see smaller trails splitting off, as you will to your left in ten minutes or less, just keep heading straight. For best results at Bear Hill, always choose the larger trail.
5. About twenty minutes from the start of the hike (walking at toddler pace), you’ll come to a fork with a “DO NOT LITTER” sign. Turn left here. (Also, don’t litter. Better yet, pick up a piece or two.)
After our hike, I inquired to Corrine about what happens if you were to turn right at this junction. She said that’s the old entrance to the preserve down that way, not another viewpoint, so you can scratch “checking out what happens if you turn right here” off your to-do list.
6. In just a few more minutes, the trail begins to ascend toward what feels like possible awesomeness.
Indeed, that’s what’s up there.
(As you leave the trail to ascend the rock face, check behind you to make note of where the trail and rock meet – you’ll need to find this spot again later, and it is possible to get disoriented with several unmarked trails departing from various points.)
7. After marinating your eyeballs in the view, look for a trail that heads back into the woods, parallel to the cliffs, to your left (assuming you’re facing the view).
Hop on that trail, and then almost immediately turn to your right, heading downhill for a moment. After that turn, off to your right, you’ll start to get a hint of the chasms to come.
8. The trail descends into a rocky bowl-shaped area, with you in the bottom of the bowl. Feel free to take a moment here to (carefully!) explore some of the interesting rocks.
9. Down at the bottom of the bowl, on the right-hand side, you’ll find a curious gap just behind a tree.
Go ahead, check it out.
10. Turn the corner and: Duuuuuuuuuuuude.
I can’t find mention of it anywhere online, but Corinne called this place the “Grapefruit Squeeze.” Or maybe “Grapefruit Squeezer”? In any event, this is a prime place to get your squeeze on.
When you get down to the bottom, there’s a field of boulders, and not much else. You’ve seen the main event, so feel free to carefully explore down here, then head back up when you’re ready.
11. After you emerge from the Grapefruit Squeeze, the great news is that there’s still more to see. Wait, MORE?? I know, get out, right?
With the entrance to the Grapefruit Squeeze at your back, walk a short way toward the trail you came in on. Instead of following that trail back up to the right, though, look to your left, and find a way up that little rock embankment (if you go almost all the way back to the trail, you’ll find an easy spot to hop on top of the embankment, much easier than the path my kids blazed in the picture below).
12. On top of those rocks, once again: duuuuuuuude. Holy cow, this place is amazing.
Take it in. Eat a granola bar. Snap some pictures. Keep your kids from falling off the cliffs.
13. When you’re done checking out the extensive views and cool rock formations all along these cliffs, retrace your steps back to the first cliff you visited today, then, with the cliff’s dropoff on your left, find the return trail straight ahead and downhill. Hop on the trail and retrace your steps back to the parking area, being sure to turn right at the junction with the DO NOT LITTER sign.
Bang! You did it! What an awesome place, right?
If you know of a better way to spend five bucks, please share it with the rest of us in the comments below. Now, who’s thirsty for some fresh-squeezed grapefruit?
Directions to the trailhead: From Walden, take Route 52 west for about 14 miles. As the road ascends steeply, keep an eye out for Cragsmoor Road on your right. Turn right onto Cragsmoor Road and follow it for about 1.4 miles, past the Cragsmoor Free Library on your left. Immediately after the library, turn left onto Dellenbaugh Road. In less than a minute, keep left at the fork (with Meadow Ln) to stay on Dellenbaugh Rd. Arrive at the well-marked entrance to Bear Hill Preserve on your left, just as a big fat view opens up in front of you. Park in the small lot, hop out and let the adventure begin!
You can also get directions by checking out the Bear Hill Preserve entry on the HiketheHudsonValley.com Google map.
Sorta nearby address for your GPS: The address of the Bear Hill Preserve is:
117 Dellenbaugh Rd
Note: Do NOT just punch “Bear Hill Preserve” into the Google Maps app (which it WILL let you do) and expect it to take you to the right place. As of late 2015, Google Maps will take you to the wrong side of the preserve, on Rt 52, where there is no entrance. I speak from experience here. Hopefully, I just saved you about 14 expletives.
GPS coordinates of parking area: 41.67214, -74.39196 (Clicking will open in Google Maps or the Apple Maps app, depending on your browser/device.)
Super-cool Google Earth flyover of hike route:
Google Terrain Map of hike route:
Related resources: If you’re looking for actual facts and/or useful information, visit these resources:
- This nice botany site that, at one time, contained the only reliable online information to find this preserve
- Some beautiful photography and a nice write-up in this post on the venerable Steve’s Digicams Forums
- Some nice user-submitted photos on the (unofficial?) Bear Hill Preserve Facebook page
- A beautiful gallery of Bear Hill photos from Gerald Berliner Photography
- I think that’s seriously it