If you find this free trail guide useful, please provide payment by picking up at least one piece of litter on your hike. Cha-ching! Thanks for being awesome! (And here’s a quick primer on Leave No Trace, too, to help us keep the trails nice and fresh for each other.)

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.

Trail Guide

Bonus unsolicited advice: Don't depend on having cell service in the woods - it can be spotty out there! Download this trail guide to your phone before you head out. (It's easy to do on iPhone and Android.) May your connection to nature be strong, even when your connection to the internet is weak.

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 Google map.

Sorta nearby address for your GPS: The address of the Bear Hill Preserve is:

117 Dellenbaugh Rd
Cragsmoor, NY

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.)

Resources & Interactives

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

Want to support trails in the Hudson Valley? Here’s one great way: Visit the New York-New Jersey Trail Conference homepage and click on Volunteer, Donate, or Shop! (Then you can volunteer, donate, or shop, depending on your mood.)

Comments (57)

Was this trail guide useful to you? Please leave a comment!
  1. Ian

    Cheapskate alert, lol, well said by an out of towner. As someone that grew up in Walker Valley this was amazing place to go anytime of day with your friends. All the local kids hung out here during and after school. Then people from outside the area came in droves and caused the b.s. fee to be instituted. So yes, many of us who spent all of of our youth going here for free. Any amount of money seems like highway robbery

    1. Mike

      Ian, yeah, I never visited when it was free, but the hike from three to seven bucks felt rather abrupt. As I mentioned on the Mohonk Mountain House trail guide: “The best things in life are free. But sometimes, the best hikes aren’t.” And the Mountain House costs $35 (each!) to hike there these days — Bear Hill is a steal by comparison! If that helps at all 🙂

  2. Terry Kristensen

    As a single hiker with a focus on both challenge and safety, this is EXACTLY the sort of information I need to plan a hike. Especially since I am just now discovering the amazing Hudson Valley area. Thank you SO MUCH for providing not only detail for the hike, but for highlighting such an inviting place! (Sorry about the caps. I would have simply italicized, but that wasn’t an option!)

    1. Mike

      Terry. thank you so much for the kind words! Even the screamy ones! (Ha, just kidding, I know the formatting options are quite limited, and think you did a great job with the tools available.) Thank you for taking the time to brighten my day — really glad you found this guide useful. Enjoy discovering all the awesome places to explore around here!

    1. Mike

      Hi, Jessica! At long last, it is indeed open again! (See Adam’s helpful comments below for confirmation.) Hope you have a great time if you go!

    2. NANcy

      Well my good friend just posted pictures of them with two other adults and 3 children of young elementary age. So as of June 6th I would say they are open!

    1. Mike

      This is really helpful, Wendy! Thanks for confirming, I was wondering if they had re-opened. I’ll leave this hike as-is on the “Hudson Valley trail closures and parking restrictions due to COVID-19” page. (I also just added a link from that page to your comment here, so hopefully people will see that it’s still closed.) Really appreciate you taking the time to share this information – thank you!

      1. Mike

        Hi Benjamin — yes, still closed. There’s a comment confirming the closure on the Alltrails page for Bear Hill Preserve dated Nov 14. Not sure when they’ll be open again, but since they never opened back up this summer, I presume it’s going to be a while. If someone finds out that they’re open again, please let us know! (And thanks in advance, helpful person from the future!)

      1. Mike

        Hi, Jillian! I believe it is still closed. Hope to see some news about it opening again, but the fact that it’s been closed for this long leads me to believe that life will have to be back to normal before it will be open again. (And if anyone hears otherwise, please let us know!)

    2. Adam L Naill

      I didn’t see how to comment so I”m just replying to Wendy. I have heard just today on Facebook that this trail is NOW OPEN.

      1. Mike

        Adam, that’s fantastic news — thank you for sharing it here! I’ve removed the **FIVE-ALARM ATOMIC-WEDGIE WARNING!!!** from the beginning of the trail guide that, until today, warned people about the trail closure. So glad this hike is open again, and really appreciate you dropping that news here! (And you can leave new comments by scrolling down to the bottom of the comment section, but your reply to Wendy’s comment got the job done just fine!) THANK YOU!!!

  3. Roman kormeluk

    When I was a kid I’d go to a Summer camp on Rt 209. We would hike straight up the mountain to what we called Bear Rock (I assume Bear Hill Preserve) It was assume visiting after being able to see the rocks from out camp below.

    1. Jeff

      Tom, there’s no gate and when I was there on Sept. 23 I didn’t see any indication that access was ever limited. A trailkeeper/money collector will likely be on duty from 10 a.m. to 5 p.m. daily, but otherwise you can leave some cash in a donation can at the trailhead (and hope some punk doesn’t poach your dough). $7 per adult, brats under 12 are free. Totally worth seven bucks each!

  4. Suzan

    I just want to thank you for this site, Mike, which made our weekend in the Hudson Valley much more fun! My husband’s knees are not what they once were, and finding easy hikes with good views was a breeze with your search functions. You’ve really provided a wonderful resource that I will happily return to the next time we venture up north (from outside Phila). If you ever feel like doing a biking site, we’d welcome it!!!
    Thanks again –

  5. Monica

    Amazing place! I wouldn’t have known it existed if not for you. Thanks! I can’t think of a hike with a more favorable effort:payoff ratio.

    1. Mike

      Thank you, Anna! I’ve updated the cheapskate alert above. Much appreciated! That’s a hefty increase from three bones in 2015. But yeah, still worth it.

        1. Mike

          Hi Katie — You caught me being purposefully vague! As I understand it, if you happen to luck out and find nobody there to take your money, that’s an off-peak time. All other times are peak. Generally speaking, I’d expect showing up on weekdays (very early or very late) to increase your chances of being there at an off-peak time. If anyone knows something more concrete, please let me know and I’ll update the trail guide accordingly!

    2. Kathy Richardson

      Thankfully my family and I were able to enjoy Bear Hill for FREE in our lifetimes, before the moneymongers arrived! It’s so sad that there is now a price to pay for observing the natural beauty of our area….

  6. Emma

    Thought you might be interested to know that one of the pictures you took is from the exact same angle as a painting from 1935 by Charles Courtney Curran – ‘Boulders on Bear Cliff’. How wonderful that it still looks the same today!

  7. Vangie

    Went here today when it’s so cold and windy but we did enjoy ourselves exploring the place. It was windy on the top by the cliff but when you go and explore the boulders which blocked the wind, we were more comfortable. Thanks for guide as always it is on point. We’re thinking of going back in the summer and do a little picnic there.

  8. Deb

    Thank you so much for this guide!! We wanted to do something near Sam’s Pointe but it was over packed as usual. This place was AMAZING, never would have found the right entrance without you!

    1. Mike

      Thanks so much, Deb! Without good directions, finding this place can be like finding the entrance to Hogwart’s. Glad you found it, and glad you had a great visit!

  9. Robin Knapp

    Dude. This was an awesome hidden gem! I was headed to Bonticou at Mohonk, but after consulting your list, changed my mind. A little drive from Catskill, but so worth it. Incredible views, even on the road up! Thanks for helping me find new places in my home, you rock.

  10. Mack

    What an amazing place! We visited today and had the place to ourselves. The helpful man at registration let us know it’s wild blueberry season and we were free to pick; we grabbed a bag from the car and are looking forward to blueberry picking tomorrow!

    1. Mike

      Sounds like you hit the jackpot, Mack! Thanks for letting us in on the secret — late July sounds like a great time to visit Bear Hill.

    1. Erica

      I would think it should be fine. It’ll definitely be cold at the overlook and there might be some ice but the hike isn’t very steep or long. I’d definitely give it a shot!

    2. Mike

      Hi, Ken! I don’t have first-hand experience visiting at this time of year (and I imagine the caves will be impassable or at the very least extremely dangerous to visit now), but according to this Gerald Berliner Photography post from Dec 15, visiting the views at the clifftop can be done. (Please note the comments in that post to see some of the safety equipment he wears to maintain traction on the cliff tops.) Happy visiting and safe travels if you give it a go!

    1. Mike

      Hi Erica! For the hike itself, I agree with Linda. If you’re going to attempt to enter the Grapefruit Squeezer (shown in steps 9 and 10 above), though, you’ll likely have to remove the pack. Mine has a wide kickstand on the back that made it impossible to wear in there. It’s very close quarters at the entrance — even if your pack does fit through, you’d have to be very careful to avoid any head-clunking or kid-smooshing situations. My recommendation would be to take off the pack and carefully guide or carry your kid(s) into the Squeezer, which is what I did, or do what my friend Sergey did, and explore the cavern by yourself while someone else (me, in this case) watches your kid up top. Hope that helps – happy adventuring!

    1. Mike

      It sure is! Dogs on leashes are welcome here. I didn’t bring mine because I was already wrangling the kids and needed to make sure they didn’t fall off the cliffs, but otherwise this would be a great place to bring a dog. We passed many pooches along the trail.

  11. Linda Kleinhenz

    Thanks! I love your entertaining commentary and great detailed descriptions/pictures. On my way to visit it for the first time!

    1. Mike

      Hi Maureen — The only relevant information I can find is this map from the NY-NJ Trail Conference. I’m not sure if the map indicates areas affected outside of Minnewaska, but if it does, that hopefully suggests that Bear Hill Preserve did not get directly affected by the fires. If anyone has more current or specific information, please share it!

  12. Kelly

    Quick update on the admission fee: it’s now $5, but if you think you’ll go at least 4 times in the next year, spring for the annual pass for $20. I think it would be a bargain at twice the price, but apparently there’s been some grumbling, so hopefully the word will get out so the volunteers don’t have to endure complaints.

    1. Mike

      Thanks so much for the update, Kelly! I’ve amended the “Cheapskate Alert” above accordingly (again), from three to five dollars. Really appreciate your help to keep this trail guide current!

  13. Jane

    Love Bear Hill Nature Preserve! Thank you for listing it– what a treasure, we needed something quick over in that neck of the woods and we arrived about 3:30pm, the little cabin was closed up. But would certainly be worth the $3 entrance fee!

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