Sugarloaf Hill,Osborn loop trail

Really nice loop to do in late fall when the leaves are down. You get awesome views of the Hudson and the trail is not terribly steep like some of the other in the area. So if you are new to hiking or are going with kids and/or pets this is a great hike to go on. The loop will bring you up to the top of Sugarloaf and then on the way down you can pass by a still running castle. While it is off limits and no trespassing is allowed you can get pretty close using some of the woods roads.

Good place

A hiking trail that takes you to Sugarloaf Hill and the Osborn Loop that starts at a very beautiful meadow with a view of Castle Rock atop the hill. There is a small parking lot where the blue trail begins. You will know you are at the right spot when you see a map of the trail right at the lot right off Wing and Wing Road. For a hike to Sugarloaf Hill, simply follow the blue trail across the meadow with a view of the castle up above. The castle is strictly private property but the view is enjoyable. When you cross the meadow, you will enter the woods as the blue trail will turn right. Continue straight as the trail slowly begins to ascend.

Continue on the the blue trail as it will end at the RED trail just ahead This is the trail that will take you to Sugarloaf Hill. Continue on the red trail as it will continue to ascend towards Sugarloaf Hill. It gets very hilly but not very steep. Continue and make sure you stay and follow the red trail markers and not into private property. As you continue up, the trail will eventually get less hilly for a little while. Continue hiking as the red trail will make a SHARP right. Pay very close attention to it or you will miss it and you will continue on to the blue trail for the Osborn Loop. In case you do, just backtrack unless you want to do the Osborn Loop.

Once you make a right and continue on the red trail, it begins to get very steep. This is the steepest and most strenuous part of the hike as you ascend closer to the summit of Sugarloaf Hill. Once you reach the top, continue on the red trail and shortly you will reach the end of the trail where it offers a great view of the Hudson River and the southern Hudson Highlands. Relax and enjoy the view. Also, please be careful not to step on the prickly pear cacti that grows there. When you're done, simply follow the trail back to where you started. :)