6
hikers
04:04
14.3km
310m
Hiking
Hike the moderate 8.9-mile Sugarloaf Hill and Osborne Loop in Hudson Highlands State Park, featuring views, historical sites, and Castle Roc
Last updated: February 26, 2026
Tips
Your route passes through protected areas
Please check local regulations for:
Waypoints
Start point
Parking
Get Directions
9.97 km
Highlight • Castle
Tip by
14.3 km
End point
Parking
Way Types & Surfaces
Way Types
10.8 km
1.75 km
1.66 km
101 m
Surfaces
8.97 km
2.72 km
1.86 km
686 m
101 m
Sign up to see more specific route details
Sign up for free
Elevation
Sign up to see more specific route details
Sign up for free
Weather
Powered by Foreca
Today
Thursday 21 May
17°C
11°C
55 %
Additional weather tips
Max wind speed: 13.0 km/h
to get more detailed weather forecasts along your route
This route was planned by komoot.
Parking is typically available at designated areas within Hudson Highlands State Park Preserve, which hosts the Sugarloaf Hill and Osborne Loop. It's always a good idea to arrive early, especially on weekends, as parking can fill up quickly.
Yes, the Sugarloaf Hill and Osborne Loop is generally dog-friendly. However, please ensure your dog is kept on a leash at all times, and remember to pack out any waste to help keep the park clean for everyone.
The trail is enjoyable in most seasons, but autumn is particularly beautiful. In the fall, the fallen leaves can create stunning vistas across the high hills. Spring and early summer also offer pleasant conditions before the peak heat.
No, there are typically no permits or entrance fees required to hike the Sugarloaf Hill and Osborne Loop within Hudson Highlands State Park Preserve.
This is a moderate hike, though some sections can be challenging. You'll encounter diverse terrain, including a short trail through a grassy meadow, and rocky areas, especially during uphill portions. Sturdy shoes are highly recommended due to the rocky and sometimes steep nature of the path.
The loop offers several notable features. You'll find good views, including a vista facing south towards the Bear Mountain Bridge. Keep an eye out for old farms, barns, and glimpses of the 'magical Osborne Castle Rock'. There's also a notable cactus grove at the dead end of the Sugarloaf Trail, a beautiful pond, and a restored gazebo. Don't miss the Castle Rock Unique Area.
Yes, the route connects with several other paths. You'll find sections of the Osborne Loop, Sugarloaf Trail, and even portions of the famous Appalachian Trail. Other trails like the Castle Rock Trail, Glenclyffe Loop, and Carriage Connector also intersect or run alongside parts of this route.
Yes, as its name suggests, this is a true loop trail, meaning you'll end up back near your starting point without having to retrace your steps.
Given the moderate difficulty and rocky sections, sturdy hiking shoes are essential. We also recommend bringing plenty of water, snacks, a map or GPS device (like komoot), and appropriate layers for changing weather conditions. Trekking poles can be helpful for stability on steeper or rocky descents.
While generally moderate, some sections can be challenging due to rocky and steep terrain. Families with younger children or those new to hiking might find it somewhat difficult. It's best suited for families with some hiking experience and children who are comfortable with longer distances and varied terrain.
To fully enjoy the experience, wear sturdy hiking shoes to navigate the rocky sections. The area is known for its quiet, remote nature, offering a less crowded experience than some other popular trails. Consider visiting in the fall for spectacular foliage and extended views.