Our 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.
This trail is part of Hudson Highlands State Park Preservein the Hudson Valley region — explore all hikes in New York.
Bear Mountain State Park, NY
Bear Mountain is probably our most-hiked trail. It's close to the city, it's beautiful year-round, and the views from the top are consistently stunning. We've brought everyone here - friends, family, even our parents - and everyone loves it.
The loop has a nice mix of everything: wooded sections, rocky paths, and some exposed ridgeline walking with incredible views. The climb to the summit is steady but never brutal. We'd call it a solid moderate - you'll work up a sweat, but you won't need to rest every five minutes.
Perkins Memorial Tower at the top is a great spot to catch your breath and take in the 360-degree views. On a clear fall day, with the autumn colors in full swing, it's honestly one of the most beautiful places in the Hudson Valley. We always pack our lunch and eat it up there.
The biggest hassle is parking. On a nice weekend, the lot near Bear Mountain Inn fills up fast. We've started arriving before 8am and that usually does the trick. After the hike, the inn area is great for grabbing food or just sitting by the lake. This trail has a special place in our hearts - it's where we first fell in love with hiking in the Hudson Valley.
See our photos from this hike on Instagram @best.hikes.usa
Start Early for Parking & Views
The parking lot near Bear Mountain Inn fills up quickly, especially on weekends. Arriving early not only ensures a parking spot but also allows you to experience the stunning vistas with fewer crowds.
Bring Adequate Water & Snacks
The loop can take 3-4 hours, so carry enough water (at least a liter per person) and energy-boosting snacks to stay hydrated and fueled throughout the hike. Refill stations might not be available along the trail.
Proper Footwear for Rocky Terrain
The trail includes rocky sections and uneven terrain. Sturdy hiking shoes with good traction are crucial for stability and preventing slips or twisted ankles. Breaking in new footwear before the hike is advisable.
Bear Mountain Inn RestaurantRestaurant
Right at the trailhead, the Bear Mountain Inn offers a great dining experience with a variety of dishes and local beers available. Relaxing atmosphere.
View in Google MapsThe Peekskill BreweryBar
Excellent selection of craft beers brewed onsite. They also have a menu featuring delicious pub-style food, making it a popular post-hike spot.
View in Google MapsThe GarrisonRestaurant
Known for its upscale dining experience. Features a farm-to-table menu, emphasizing fresh and seasonal ingredients. Beautiful view of the Hudson River.
View in Google MapsAppalachian Trail CafeCafe
Located in nearby Cold Spring. Offers a more casual dining experience with a variety of options such as sandwiches, salads, and coffee. Popular spot for hikers and locals.
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
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.
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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