This is going to be one of those great fall hikes that stays under the radar and away from crowds. There’s plenty to explore in this network of trails that connects with the Appalachian Trail in the lower Hudson Valley.
Castle Rock Unique Area is a 129-acre property in Garrison, New York that includes the Sugarloaf Hill hike. The castle is the estate of William H. Osborn who served as president of the Illinois Central Railroad. It was built in 1881 to be used as a summer house for the Osborn family and later passed down to the children. Much of the property including Sugarloaf Mountain was donated to the Department of Environmental Conservation and the remaining land was purchased. The castle however remains as private property and was added to the National Register of Historic Places in 1977.
About The Hike
The hike starts by going through a field with old barn and pump house structures before entering the woods and climbing up hill. Upon the hill you’ll see the Castle Rock estate which is the best ‘view’ you’ll actually get of the castle during the hike.
After a mile along the trail there is split to Sugarloaf Hill, a small summit with southern views to the Bear Mountain Bridge. The trail has two additional splits using the blue Osborn Loop Trail, the path towards the right will be a substantial sized loop while the other is more moderate, maybe only a couple of miles.
Both loops hook into the Appalachian Trail and use it to connect back to the Castle Rock Unique Area land. There are a couple marked and unmarked carriage routes through the park to be explored and two Gazebos along the way.
The unmarked carriage routes will take you towards the Castle Rock private property. The castle had previously been left abandoned and unoccupied for years however it is currently going through renovations. There are plenty of no trespassing signs in the area but also plenty of workers making it tough to bypass.
The best AllTrails link for this hike is the climb up Sugarloaf Hill, details and link below.
Sugarloaf Hill Trail:
Distance: 2.9 Miles
Type: Out & Back
Elevation: 738 feet
Total Ascent: 656 feet
AllTrails Link – Sugarloaf Hill Trail
Getting There and Important Information
The parking lot for Castle Rock Unique Area is along Route 9D, the turn into Wing and Wing Road is between the two stone pillars. The lot fits about 6 cars making this hike perfect for a more secluded type of feel.
No admission fee for park or use and on the DEC website it says primitive camping is allowed, plenty of better camping spots but could be cool? (I didn’t see anywhere that would be good however)
You’ll see plenty of signs stating the Castle and Castle Road are private property and hikers are not permitted. These are probably best to obey with the amount of renovation going on.
If you’re looking to connect onto the Appalachian Trail for a hike in this area, be sure to check out my write up on this section in my 10 Favorite Sections of the Appalachian Trail post!
10 Favorite Sections of the Appalachian Trail
Looking to explore other hikes in the area? Check out some of these!
©Copyright 2020-2021 Secret Hike
Photography exclusively by Dan Oliver unless otherwise stated and cited. Embedded maps are provided by Embed Google Map (embedgooglemap.net) and map images shown are provided as stated and cited.
This website is provided for entertainment purposes only, and is not meant to serve as an instructional guide, or present itself as an authority for any of the locations written about. The locations mentioned, written, and photographed herein are nothing more than my personal adventure archive. If you are interested in visiting any locations you should not depend on the information in this website to plan any excursions. You should research a wide variety of informational sources, websites, hiking guide books and maps found elsewhere. Many locations are dangerous and potentially illegal to access which can lead to fines, injury or death even when prepared. I do not encourage anyone to trespass or put themselves or others in way of harm. This website, and therefore its’ owner/author, cannot assume any responsibility for anything you may incur while hiking or exploring any of these locations or anywhere on planet earth. Thank you for viewing!