This 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.
This trail is part of Hudson Highlands State Park Preservein the Hudson Valley region — explore all hikes in New York.
Mohonk Preserve, New Paltz, NY
This loop at the Mohonk Preserve is one of our favorites - a trail with two personalities. The Undercliff section takes you beneath towering cliff faces through a cool, shaded corridor. Then the Overcliff section brings you up top with sweeping views of the valley below. It's like getting two hikes in one.
The trail is about 5 miles and moderately challenging. There are some rocky sections and elevation changes, but nothing that should worry a reasonably fit hiker. We found the terrain varied enough to keep things interesting the whole way.
The cliff-edge views from the Overcliff portion are spectacular. We stopped at several overlooks and each one seemed better than the last. On our fall visit, the foliage was so bright it almost looked unreal. This is definitely one of those trails where you'll burn through your phone's camera roll.
The path is generally well-marked, though we'd recommend paying attention at the transition points between the two trail sections. Arrive early for parking, especially during fall foliage season - the Mohonk Preserve is popular for good reason. We love this hike for a half-day outing when we want something beautiful without a massive commitment.
See our photos from this hike on Instagram @best.hikes.usa
Terrain Awareness
Be prepared for rocky sections and some elevation changes along the trail. Wear sturdy hiking shoes with good traction to navigate these areas comfortably.
Scenic Overlooks Timing
Plan your hike to enjoy the scenic overlooks, especially during sunrise or late afternoon to capture breathtaking views of the Hudson River. These times often offer incredible lighting for photography.
Trailhead Parking
Arrive early to secure parking as spaces might fill up quickly, especially on weekends. Consider carpooling or arriving during off-peak times to find easier parking access.
Trail Etiquette
The Undercliff Trail can get busy at times. Be courteous to fellow hikers by yielding on narrow sections and maintaining a considerate distance to respect others' experiences.
Foliage Season
During fall, the trail offers stunning foliage views. Consider hiking during peak foliage for an extra vibrant and colorful experience, but expect increased trail traffic during this popular season.
Cold Spring DepotRestaurant
Historic restaurant housed in a former train station offering a diverse menu and a great selection of craft beers. Great outdoor seating.
View in Google MapsThe Foundry RoseCafe
Breakfast, brunch, and lunch at the former Foundry Cafe location. Open since 2024 with a rotating menu and dining events.
View in Google Maps
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.
View Trail
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.
View 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.
View TrailThese are the items we bring on every hike. Links help support this site at no extra cost to you.
Rocky, rooted trails in the Northeast need real ankle support.
We use: Merrell Moab 3 Mid WP
Bring at least 2 liters. Most trails here don't have safe water refill points along the route.
We use: CamelBak Chute Mag 32oz
Fits water, food, rain layer, headlamp, and a basic first aid kit comfortably.
We use: Osprey Talon 22
The rocky ridges here — especially on descents — are much more manageable with poles.
We use: Black Diamond Trail Ergo Cork
Trail forests get dark fast. Always carry one even on planned half-day hikes.
We use: Black Diamond Spot 400
Northeast mountain weather is unpredictable. Afternoon storms roll in without warning — always have a packable layer.
We use: Marmot PreCip Eco Rain Jacket
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