This trail goes from one side of the park to the other and is a wonderful sampler platter of all the Hudson Valley has to offer a hiker. This trail runs concurrently with the Appalachian Trail here and there but leaves the AT occasionally to offer more solitude and avoid the crowds at Bear Mountain.
Enjoy alpine-like bald summits of glacially-scoured bedrock, views of lakes and streams, bogs and wetlands, and finally, commanding views of the Hudson River from north to south as well as nearby Bear Mountain. This trail will test your endurance but offers a wide variety of landscape features and views.
Convenient access can be had from the Tuxedo train station. From the trailhead, climb up towards the secret hideout of Claudius Smith, a revolutionary, war-era outlaw who made his hideout in the cave just east of the hill that bears his name on the USGS maps. Some refer to the cave itself as Smith Rock, but check it out either way. The detour is worth it!
You'll need to make a left to stick with this trail, but from there you'll continue on. Ascend Black Ash mountain for a great view of Lake Sebago, and continue north across a road to a unique rocky area scraped by glaciers and littered with boulders. After a while, you'll rejoin the Appalachian Trail and travel over a long, LONG series of hills and valleys, eventually crossing the Palisades Parkway
You are now in Bear Mountain State Park, but the next big mountain is Dunderberg Mountain, which offers great views of the park's namesake peak. Enjoy the fact that you have just traveled clear across the Hudson Highlands!