We 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.
This trail is part of Hudson Highlands State Park Preservein the Hudson Valley region — explore all hikes in New York.
Overlook Mountain Road, Woodstock, NY
Overlook Mountain is a Catskills classic and we've hiked it more times than we can count. The draw is the fire tower at the top - climb those stairs and you get a jaw-dropping 360-degree view of the Hudson Valley and the surrounding peaks. On a clear day, you can see forever.
The trail is about 4.6 miles round trip and follows an old road bed, so it's wide and straightforward. The climb is steady - 1,370 feet of elevation gain - so you'll definitely feel it in your legs, but there are no tricky scrambles or technical sections. Just put one foot in front of the other and keep going.
Along the way, you pass the ruins of the Overlook Mountain House hotel, which is really cool. The crumbling walls and empty windows have this eerie, beautiful quality. We always stop for photos here. It's a great conversation starter about the area's history.
The trailhead is right in Woodstock, so combining the hike with a visit to town makes for a perfect day out. We like to grab breakfast at one of the cafes in town before hitting the trail, then come back for a beer afterward. A few notes: there's no water on the trail, so bring plenty. And the upper sections are exposed, so sunscreen and a hat are smart moves.
See our photos from this hike on Instagram @best.hikes.usa
Start Early
Begin your hike early in the day to avoid crowds, especially during weekends or peak seasons. This ensures a quieter experience and ample time at the summit without rush.
Bring Ample Water
Carry plenty of water, especially on warmer days. There are no water sources along the trail, so staying hydrated is crucial. A reusable water bottle or hydration pack is recommended.
Sturdy Footwear
Wear sturdy hiking boots with good traction. The trail can get rocky in sections, so proper footwear will provide stability and prevent slips on uneven terrain.
Sun Protection
Bring and apply sunscreen, and consider wearing a hat and sunglasses. Much of the trail is exposed, especially near the summit, so protection against sun exposure is vital.
Camera or Binoculars
Don't forget your camera or binoculars! The views from the fire tower are exceptional, and you might catch sight of wildlife or distant landmarks. Capture the moments and enjoy the scenery.
The Catskill Mountain Country StoreStore
Charming spot offering a deli and a variety of local snacks. Good place to grab a refreshing drink and some delicious post-hike snacks.
View in Google MapsHunter Mountain BreweryBar
Brewery offering a range of craft beers perfect for winding down after a hike. Pair your brew with their selection of pub-style food for a satisfying post-hike meal.
View in Google MapsDeer Mountain InnRestaurant
Worth the visit for a more upscale dining experience. Features a restaurant serving farm-to-table cuisine and a selection of beverages to relax and rejuvenate after your hike.
View in Google MapsLast Chance Antiques & Cheese CafeCafe
Quirky spot offering a unique combination of antiques and a cafe with a selection of beers. A charming place to relax and grab a drink after your hike, along with some light bites or sandwiches.
View in Google MapsTaconic DistilleryBar
Distillery offering a fantastic selection of handcrafted spirits. They specialize in bourbon and rye whiskey, providing tastings and tours for visitors.
View in Google MapsCatskill Distilling CompanyBar
Distillery offering a range of spirits including whiskey, gin, and vodka. They often have tastings and tours available for guests to learn about their distillation process.
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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