This is probably where we hike the most. Over 7,000 acres of trails right along the Hudson River with dramatic cliffs, forested ridges, and multiple summits. Breakneck Ridge is the headliner, but there are so many other great trails here that don't get nearly enough attention. We love that you can piece together different routes and never do the same hike twice.
EasyA beautiful section of the Appalachian Trail near Pawling, NY that takes you through open meadows, rolling farmland, and along a boardwalk through the Great Swamp. One of the more unique AT sections in New York - feels more like the English countryside than a mountain trail.
ModerateShort but solid. 2.6 miles with enough elevation to feel like real hiking. Steady climb through woods with rocky sections. Views of the Hudson River at the top are perfect - we've done this one a bunch of times and never get tired of it.
ModerateOur most hiked trail. Mix of woods, rocky sections, and ridge walking with incredible views. Summit tower gives you 360-degree views of the Hudson and surrounding peaks. Solid moderate difficulty - you work but never feel destroyed. Close to the city, beautiful year-round.
ChallengingIntense. 3 miles of steep scrambling with hand-over-hand climbing. Rock exposure and serious terrain. Only for experienced hikers comfortable with climbing. But the views of the Hudson River are absolutely worth it if you're ready for the challenge.
ModerateOne of our favorites near Cold Spring. 5 miles with real views of the Hudson River from the summit. Mix of woods, open meadows, and rocky sections. Good workout without being brutal. Close to the city so it gets busy on weekends.
ModerateA 7-mile loop from North-South Lake through some of the best scenery in the Catskills. Follows the Escarpment Trail to North Point for panoramic Hudson Valley views, descends to Ashley Falls, then loops back along North Lake Road. A perfect mix of cliff-edge views, waterfalls, and lake beach to finish.
ModerateA moderate out-and-back to one of the best cliff-edge viewpoints in the Catskills. The trail ends at a massive exposed rock ledge overlooking the Kaaterskill Clove with views stretching out for miles. Less crowded than the popular Kaaterskill Falls trails nearby.
Challenging7 miles with 2,000 feet of elevation gain. Definitely earns its views. The Indian Head overlook is breathtaking - the valley just opens up below you. Rocky terrain and steep sections, so sturdy boots are a must. Solid challenge with major payoff.
ModerateA short but steep climb to one of the best Hudson River viewpoints in the area. Under 3 miles round trip but the views from the rocky ledge at the top are incredible. A hidden gem that most people drive right past.
ChallengingSteep climb to an old fire tower with incredible 360-degree views of the Hudson Valley. The Casino Trail is relentless but short - you gain serious elevation fast. Fire tower at the top is the cherry on top. One of the best view-to-effort ratios in the area.
ModerateWe hike this one constantly. 4.6-mile steady climb on an old road bed to a fire tower with amazing views of the Hudson Valley and Catskill peaks. Pass ruins of the old hotel on the way up - cool piece of history. No water on the trail so bring plenty.
ChallengingTallest peak in the Catskills. 6.6 miles with real elevation gain and legit steep sections. Mostly through dense forest, summit is wooded but viewpoint just below has great panoramic views. Planning early, bringing layers, and lots of water is key.
ModerateThis loop has two sides - the Undercliff section is cool and shaded under cliff faces, then Overcliff brings you up top with valley views. 5 miles, moderately challenging. Like getting two different hikes in one. Fall colors are especially good here.
ChallengingIntense. 3 miles of steep scrambling with hand-over-hand climbing. Rock exposure and serious terrain. Only for experienced hikers comfortable with climbing. But the views of the Hudson River are absolutely worth it if you're ready for the challenge.
Challenging7 miles with 2,000 feet of elevation gain. Definitely earns its views. The Indian Head overlook is breathtaking - the valley just opens up below you. Rocky terrain and steep sections, so sturdy boots are a must. Solid challenge with major payoff.
ChallengingSteep climb to an old fire tower with incredible 360-degree views of the Hudson Valley. The Casino Trail is relentless but short - you gain serious elevation fast. Fire tower at the top is the cherry on top. One of the best view-to-effort ratios in the area.
ChallengingTallest peak in the Catskills. 6.6 miles with real elevation gain and legit steep sections. Mostly through dense forest, summit is wooded but viewpoint just below has great panoramic views. Planning early, bringing layers, and lots of water is key.
ModerateShort but solid. 2.6 miles with enough elevation to feel like real hiking. Steady climb through woods with rocky sections. Views of the Hudson River at the top are perfect - we've done this one a bunch of times and never get tired of it.
EasyA beautiful section of the Appalachian Trail near Pawling, NY that takes you through open meadows, rolling farmland, and along a boardwalk through the Great Swamp. One of the more unique AT sections in New York - feels more like the English countryside than a mountain trail.
ModerateOur most hiked trail. Mix of woods, rocky sections, and ridge walking with incredible views. Summit tower gives you 360-degree views of the Hudson and surrounding peaks. Solid moderate difficulty - you work but never feel destroyed. Close to the city, beautiful year-round.
ChallengingIntense. 3 miles of steep scrambling with hand-over-hand climbing. Rock exposure and serious terrain. Only for experienced hikers comfortable with climbing. But the views of the Hudson River are absolutely worth it if you're ready for the challenge.
ModerateOne of our favorites near Cold Spring. 5 miles with real views of the Hudson River from the summit. Mix of woods, open meadows, and rocky sections. Good workout without being brutal. Close to the city so it gets busy on weekends.
ModerateA 7-mile loop from North-South Lake through some of the best scenery in the Catskills. Follows the Escarpment Trail to North Point for panoramic Hudson Valley views, descends to Ashley Falls, then loops back along North Lake Road. A perfect mix of cliff-edge views, waterfalls, and lake beach to finish.
ModerateA moderate out-and-back to one of the best cliff-edge viewpoints in the Catskills. The trail ends at a massive exposed rock ledge overlooking the Kaaterskill Clove with views stretching out for miles. Less crowded than the popular Kaaterskill Falls trails nearby.
Challenging7 miles with 2,000 feet of elevation gain. Definitely earns its views. The Indian Head overlook is breathtaking - the valley just opens up below you. Rocky terrain and steep sections, so sturdy boots are a must. Solid challenge with major payoff.
ModerateA short but steep climb to one of the best Hudson River viewpoints in the area. Under 3 miles round trip but the views from the rocky ledge at the top are incredible. A hidden gem that most people drive right past.
ChallengingSteep climb to an old fire tower with incredible 360-degree views of the Hudson Valley. The Casino Trail is relentless but short - you gain serious elevation fast. Fire tower at the top is the cherry on top. One of the best view-to-effort ratios in the area.
ModerateA loop around a pristine lake with a wild history - it was once a nuclear research facility. Now it's a peaceful hike along the Appalachian Trail with a crystal-clear lake, rolling hills, and one of the most unique backstories of any trail in New York.
ModerateWe hike this one constantly. 4.6-mile steady climb on an old road bed to a fire tower with amazing views of the Hudson Valley and Catskill peaks. Pass ruins of the old hotel on the way up - cool piece of history. No water on the trail so bring plenty.
ChallengingTallest peak in the Catskills. 6.6 miles with real elevation gain and legit steep sections. Mostly through dense forest, summit is wooded but viewpoint just below has great panoramic views. Planning early, bringing layers, and lots of water is key.
ModerateThis loop has two sides - the Undercliff section is cool and shaded under cliff faces, then Overcliff brings you up top with valley views. 5 miles, moderately challenging. Like getting two different hikes in one. Fall colors are especially good here.