A Visit to Castle Rock

Nothing beats asking what you’re supposed to be scouting for, and being told: “Castles.”

Castle Rock 01

If you’ve ever driven along Route 9D in Garrison, New York, you may have seen it from the road: a fairy tale-like castle poking out from the trees at the top of a mountain:

Castle Rock 02

Built in 1881, Castle Rock was the estate of Illinois Central Railroad president William Osborn, who also owned hundreds of acres of land surrounding property. Since Osborn’s death in 1894, Castle Rock has passed down through numerous Osborn generations and is still privately owned by the family. Rumors abound that the castle was writer Frank Baum’s inspiration for the castle in the Wizard of Oz (Castle OSborn?).

Castle Rock was deemed a National Landmark in 1977. Most of the surrounding woodland was donated to the State Parks Council and is now open to the public. Several films and TV shows have been shot at Castle Rock, and the owners are very film friendly. I was graciously granted permission to post these pictures to help spread the word, and if you’re seriously interested, email me your production interest, and I’ll pass along the contact info.

The drive up to the property is a long, windy dirt road that snakes up the mountain, a perfect approach to such a unique place. Note the numerous KEEP OUT signs! This is still private property, and a caretaker living on the premises has had to call the police countless times. Most productions park their trucks at the nearby library and use stakebeds to portage up equipment:

Castle Rock 03

When you finally get to the top of the hill, you pass under this beautiful stone arch:

Castle Rock 04

Continue around a bend, and you find a stone gate:

Castle Rock 06

Pass through and you’ve reached Castle Rock!

Castle Rock 07

The front of the castle:

Castle Rock 08

A tower:

Castle Rock 09

A different view from the lower level:

Castle Rock 10

One of many porches:

Castle Rock 11

The famous spire:

Castle Rock 12

A basement-level passage:

Castle Rock 13

This addition was to be a recreation room. Sadly, it was never finished:

Castle Rock 14

Castle Rock is currently in the midst of some serious interior renovation work. The original door has been temporarily removed for construction. Anyone know what those hooks to the right are (perhaps for tying up horses)?

Castle Rock 15

This is the front hall, and you can see the extent of renovation work. This is all to be redone within the next year or two, but a clever production company with a budget could easily cover up the work (or even help finish it):

Castle Rock 16
(pan: click for full size!)

A second room with wood-paneling:

Castle Rock 17

The living room features a wrap-around porch…

Castle Rock 18

Head out on the porch and you are treated to one of many gorgeous views of the Hudson…

Castle Rock 19
(pan: click for full size!)

The full view of the Hudson from Castle Rock:

Castle Rock 20
(pan: click for full size!)

If you look north up the Hudson, you can see West Point. From this vantage point, it becomes quite obvious why the original garrison was built on this strategic crook in the river:

Castle Rock 21

Other Castle Rock porches and balconies, all with equally stunning views:

Castle Rock 22

A lower-level porch:

Castle Rock 23

No visit to Castle Rock is complete without a trip to the famous spire. I headed up the creaky spiral staircase…

Castle Rock 24

…up into the spire…

Castle Rock 25

…which features a full panorama of windows.

Castle Rock 26

Here is the view from the spire:

Castle Rock 27
(pan: click for full size!)

Another picture:

Castle Rock 28

A rare view of the Castle Rock roof:

Castle Rock 29

Outside, the Castle Rock grounds are tree-lined, shady and peaceful. This road leads over the stone arch I passed under when I first came up the mountain:

Castle Rock 30

Looking away from the house, the road leads to a quiet spot surrounded by trees…

Castle Rock 31

At the far end is a fountain that I imagine hasn’t been used in quite a while:

Castle Rock 32

The fountain up-close:

Castle Rock 33

Finally, I love the break in this little stone wall, leading off into the surrounding wilderness.

Castle Rock 34

There’s a lot more to Castle Rock that I didn’t have a chance to shoot, including the Osborn’s original spring-fed wooden water tank. You can’t find a more unique property than Castle Rock, and the fact that it is located just over an hour from New York City is unbelievable. A special thanks again to Castle Rock for letting me post these pictures, and again, if you’re interested, send me an email and I’ll relay the contact info.


If you enjoyed reading this post, would you consider making a donation to help me make my first movie? The goal is $50,000, and to date, 1,728 Scouting NY readers have donated $36,348! Just $5 or $10 can make a difference - AND you get this snazzy Scouting NY sticker/magnet as a Thank-You gift! Click here to donate today!


And hey, if you've made it this far, why not follow us via RSS, Twitter, Facebook, Instagram, or Tumblr?


  1. Wow. Its so strange to see this up here on your blog and I never really knew of its history. I use to be friends with the Osbourne’s son and would stay over. We use to play lazer tag around the whole house. Truly fond memories of that place. Thanks for sharing and I love your blog!

  2. WOW. Beautiful. I really love that fountain! Thanks to you (and to the owners) for these amazing photos.

  3. Haha! I shot there about 4 years ago. The caretaker, Chip, was amazingly friendly.

  4. Wow, thank you for sharing this! I have passed this place 1,000 times over the years. It’s pretty great to finally get as peek at what is up at the end of that long drive.

    I *think* I remember hearing a rumor back in the mid 90s that Sylvester Stallone had bought it or lived there. Obviously that was just a rumor.

    Great stuff – Love your blog!

  5. Love your blog, and I’ve always wondered what that was up there! If you’re still scouting castles, I might suggest you travel a little farther north to Proctor, VT (just outside Rutland) and check out the Wilson Castle. No idea how they might feel about film crews, but it couldn’t hurt to ask. http://www.wilsoncastle.com/index.htm

  6. I could swear they shot (at least some of) Last Days there.

  7. I’ve hiked many times in the surrounding state parks and had always wondered what the Castle looked like up close. Thanks for giving me the opportunity to see it at last!

  8. Watch Last Days by Gus Van Sant. We shot half the movie there. Cheers to Chip!

  9. Other castles in that vicinity that might or might not be interested in film work are Lyndhurst, a National Historic Landmark in Tarrytown, and Morningthorpe, owned by the Delancey Street Foundation, in Brewster. I’d love to see either or both of them show up on the big screen one day.

  10. My husband was Alexander Perry Osborn III. He grew up at Castle Rock as it was left ot his father. He lived in Wyoming for quite some time where we met and later married. I had the opportunity to go back there about 2 weeks ago with my son Alexander Perry Osborn IV. It had been 27 years since our last visit there. Castle Rock looked a lot different then. I would really love to see it restored and made into a museum or some type of historical place. There is a lot of history there. Chip was filling us in on a lot of it when we were back there recently. My husband passed away 2 years ago and I know he dearly Loved Castle Rock.
    Lola Osborn

    • Alexander Perry Scott

      Am interested in collecting information on your family. AP Osborn descended from the younger son of Christopher Raymond Perry and Sarah Wallace Alexander (hence your late husband’s, your son’s and my name). I descend from their second son Raymond.

    • Hi Lola! My mother -in-law was Mary Steele Osborn, and spent her summers at the Castle with her grandfather, Henry Fairfield Osborn the paleontologist. Her brother was your husband’s father. I’ve been there a few times, and it is quite run down – wouldn’t it be a great museum space?

  11. I spent a wkend here in spring of 81. We had sailed up from Fort Lauderdale and spent some time in NYC with me mate’s sister and friends, who invited us to the castle for a wkend party. we sailed up and spent the wkend. I had so much fun I jumped ship and hitched back to NYC to hang out with my new friends.
    This fall my eldest son will be starting school at Bard, just up the river from Garrison. Hope to visit the castle this august when we take him to Bard. I believe Chip was the caretaker back in 81-were you friends with the folks who had just put together the John Lennon bio right after he died?

  12. I love the pics,thanks.I drove up there one day years ago with my wife and kids.We didnt get out or anything,but that caretaker came out and sent us out.He was very much a New-Yorker,very rude.A real ass.

  13. my father was the caretaker at forest farm in garrison mr osborns estate at the foot of the castle we lived there for years and i was never up to the castle it was nice seeing the pictures. are there any pictures of the house and gardens and pool and walk that mr osborn lived in?

  14. For several years I would drive by the castle on my way to Garrison Station. Looking at the castle ever morning from a distance, I felt like it was a doorway into a ‘magical world’. It was wonderful to come across your site. It gave me a chance to see the magical mystery. Thank You!

  15. i had the pleasure of visting a some years back and Chip was wonderful. i watched Last Days recently and was so excited when i figured out that i had been there. thanks for the lovely pictures. i took several while there but lost all of them 🙁

  16. I visited Castle Rock just over 20 years ago and Chip was the caretaker, even then. He was also amazingly warm and friendly. I have often thought about taking my kids up there to see it and to meet Chip. Does anyone know if he is still the caretaker now (2012)?

  17. Though it’s years after you posted this, thank you! I work at The Thayer Hotel at West Point and our hotel is directly across from the castle. People are always asking me “what that house is” and now I have the knowledge to tell them!
    Thanks Scout!

  18. This place was part of my childhood when me and my father visited the castle and Chip. I loved to hike around the castle and look out from the peak. For anyone who’s wondering Chip is still the caretaker…hes also my uncle 🙂

  19. Wow I can’t believe my mom excluded us from the comments. I am an adopted child of AP the 3rd, he adopted 3 boys and 1 girl before having his biological child with our mother. So there a 4 boys total that carry this family’s name. I would be delightfully interested to research the family history, just to set the record clear, I am related to the Osborn’s due to adoption, but it has always been my understanding you have to be a blood relative to be accepted by this family, as per my mom forfeiting the info about us and only bringing up the biological child. My oldest brother also accompanied her on her trip there to the castle the second time. Anyways, just blew my mind when I ran across this thing researching our family history with our children!!!!!

  20. And I do remember a conversation between my grandma and dad about Stallone wanting to rent the place, story is our grandma was able to meet Stallone due to this, and she expressed her disbelief about his height. Is it true, I couldn’t tell ya, but I never knew that lady to be a liar.

    • Alexander Perry Scott

      I have a lot information on the Osborn family that I am willing to share with you. Please get in touch with me at apscott1949 at yahoo.com.

  21. Very cool location. I love visiting your blog to see all the secrets parts of NYC.

  22. Hi,
    Just have this info.. My father owned Putnam Upholstery, 79 Main Cold Spring NY. His store was opened from 1958 until 1989. He restored antique furniture, wood carving, practically anything old made out of wood. He was a master craftsman. He was also a very talented at upholstery, his attention to detail and perfection, kept him very busy. This was a second his job, but his true passion and hobbie. His work spoke for itself, advertisement was by word of mouth. He did work for many famous people from White Plains, Garrison all the way to Rhinebeck NY. I meant a lot of famous people during the 1960’s & 1970’s while helping him. I could probably, write a book! The Old Money Rich and Celebs (of that Era ) were very different from everyday people in 2015.
    He worked for the Osborn Family during the mid to late 1960’s. I could be wrong, but I seem to remember my father told me there were (seven) different Osborne homes/estates in Garrison. I remember helping him lug upholstered furniture and other repaired furniture into different Osborn homes, including the Castle. Two vivid memories remain with me. In 1967 my dad and I had to go to the castle to deliver two overstuffed arm chairs and matching ottomans. They were covered in in blue and gold striped silk. We had to carry these up the stairs to Mrs. Osborn’s sitting room. I was nine years old, but big for my age, I cannot tell you how hard it was handling the slippery silk chairs up the stairs. I did not see or meet (Thee) Mrs. Osborn of that time,(but I sure did hear her). After we got the last piece up the steps I was told to wait down stairs, on my way down, I herd her Yell “Well Mr. Lucas did you pick up my scotch on your way here as I’ve asked.” He replied that he forgot because he was running late with other deliveries. Wow Mrs Osborne was beyond pissed off. She then stated,”be that as it may Mr. Lucas, We will inspect the chairs now”. By then I was standing a room with french doors, An older gentleman appeared, and asked me if I would like to see West Point and the bridge. I didn’t get his name but he took me thru a set of the french doors and onto a large slate covered terrace. The view was magnificent. When dad and I got back into the truck, I asked him about the scotch. He just said after working for the Osborn’s that lived in the castle a couple of times, He received a call, and was told not to pick up any type of liquor if Mrs.O asked or even demanded something. He told me he had to write off that bill after 120 days, 4 months of bills. Mrs Osborn sent his bills back indicating ” work not satisfactory, something missing ? ” We laughed, and assumed it was the scotch. He finally did get paid, but the check was signed by the Osborn’s bank, or accountant. My dad wasn’t worried, he just told me that’s the way the rich stay rich, they wait until they can pay you with the monthly interest on the principle. My father knew he would get paid. By the way the castle was in excellent shape when I was there. It looked like a picture out of Architectural Digest. When we drove up into the driveway that day, the fountain was working and there was a small horse drinking out of it, the horse was tide to a post close by.

    I also accompanied him on another delivery, My father said it was to another member of the Osborn family. I recall we passed the entrance to the castle went around a winding turn about one or two miles on same road towards peekskill. We made a sharp left and climbed a very long steep driveway. We passed thru two high stone gate posts. unto a flat driveway. For whatever his reason, my dad told me the Osborne brother that lived here re-modeled this castle? My recollection was of a very large home of two stories. Close to the drive way entrance there were large cut stones neatly piled in squares about 4ft high. I will never for get the entrance hall. A maid answered the door, and asked us to wait inside.This hall looked like a slightly smaller version of Grand Central Terminal. On the far side directly across from the entrance door was a double marble staircase. There was a gold painted elevator in the middle of each stair case. The floor was white marble tile as well as columns along the walls on each side of the room. I could not say much else about what was in the room. My attention went to A very old couple that appeared on a landing of the stair case. I assume that this was Mr.& Mrs. Osborn, the gentleman came down in the elevator, and lady rode an electric chair down the left stair case. It took them a little time to meet us. I remember both of them making a big fuss over me, they offered me refreshments etc. I did not need to look at my father to know I had to say (no thank you). We all went off to a side room, sort of a study or library. My father talked to them for over an hour and left his fabric sample books. I spoke only when spoken to. I really wanted to run in that big hall and ride on that elevator! What sticks in my mind is how big that hall was. My father and I were so many large homes back then, too many to count.

    My wife and I are fairly well traveled, we have toured every estate in the Hudson Valley, all the estates in Newport Port Rhode Island,starting way back in 1978. We have been to many homes and estates in California including Hearst Castle. We have toured all the Vanderbilt homes including the largest ( Biltmore), We were even the on the first tour of Delores Dukes home when it was opened to the public. We have also been on tours in Europe. We both love the Architecture. I still have never seen a home that made that much of an impression on me.

    My Father liked the Osborn family very much, not just for the work either. His day job was at IBM, and later Chemprene. He especially liked the older couple they would talk for hours on end. He received Christmas Cards from them right up until the early 1970’s.. I have not lived in New York for over 11 years now, we prefer the coast in NC. less the sharks of course! I remember when MGM made the movie Hello Dolly in Garrison and Cold Spring, in 1969. I also remember some of the homes that are tucked away in the mountains off of rt 306, and the road that runs under the bridge on RT.9D just outside of Cold Spring by the old Butterfield Hospital. I think it runs all the way thru to route 52 in Fishkill NY.

  23. Love everything about this CASTLE! I worked directly below and across at the Highlands Country Club. Such a beautiful site to see during break time! Now that I see the close ups and inner art of the building, I believe I’m inspired to create my own Painting of this Beautiful Location!!!