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Routes
Hiking trails & Routes
Putnam County

Sugarloaf Hill and Osborne Loop

Routes
Hiking trails & Routes
Putnam County

Sugarloaf Hill and Osborne Loop

Moderate

6

hikers

Sugarloaf Hill and Osborne Loop

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:

Castle Rock Unique Area

Waypoints

A

Start point

Parking

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1

9.97 km

Castle Rock Unique Area

Highlight • Castle

Castle Rock Unique Area is a large estate that was owned by the president of the Illinois Central Railroad company as a summer home. Much of the land of the …

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B

14.3 km

End point

Parking

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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

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Elevation

Elevation

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Weather

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Today

Thursday 21 May

17°C

11°C

55 %

Additional weather tips

Max wind speed: 13.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access the Sugarloaf Hill and Osborne Loop?

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.

Is this trail dog-friendly?

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.

What is the best time of year to hike this loop?

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.

Are there any permits or entrance fees required for this hike?

No, there are typically no permits or entrance fees required to hike the Sugarloaf Hill and Osborne Loop within Hudson Highlands State Park Preserve.

What is the difficulty and terrain like on this loop?

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.

What are the main points of interest and viewpoints along the route?

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.

Does the trail connect with other well-known paths?

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.

Is the Sugarloaf Hill and Osborne Loop a true loop trail?

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.

What should I bring for this hike?

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.

Is this trail suitable for families?

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.

Are there any specific recommendations for tackling this trail?

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.

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