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United States
New York
Orange County

Tuxedo Park

The best walks and hikes around Tuxedo Park

By Fede from komoot

·

Updated June 1, 2026

If you've ever tried planning hiking around Tuxedo Park, you know how quickly the options can become overwhelming. With so many trails crisscrossing the region, it's tough to tell which routes are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has explored, mapped, and reviewed hundreds of routes here, so we've done the legwork to bring you a curated shortlist of the very best.

Hiking around Tuxedo Park truly feels like stepping into a wild, forested escape. Expect dense woodlands, rolling hills, and a surprising number of serene lakes, all within the larger Harriman State Park and Sterling Forest State Park areas. The terrain offers everything from gentle lakeside strolls to more challenging climbs up low peaks, making it accessible for a wide range of abilities.

If you're looking for a classic, well-loved experience, we'd start with the Claudius Smith's Den Short Loop, a moderate 6.3 miles (10.1 km) trail that delivers a great payoff for its effort. For something a little more relaxed, the easy Claudius Smith Den and Lake Skenonto Loop at 7.2 miles (11.7 km) offers beautiful lakeside views. With more than 1,400 hikers having already explored these trails with komoot, you're in good company.

If you only do 3 of these routes

  1. 1

    Tuxedo-Mount Ivy to Triangle Loop
  2. 2

    Ramapo Dunderberg and Triangle Trail Loop
  3. 3

    Claudius Smith's Den Short Loop

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Tuxedo-Mount Ivy to Triangle Loop

13.4 km

380 m

Moderate

Ramapo Dunderberg and Triangle Trail Loop

20.1 km

700 m

Hard

Claudius Smith's Den Short Loop

6.92 km

240 m

Moderate

Ramapo-Dunderberg Trail to Tom Jones Shelter

6.93 km

340 m

Moderate

Claudius Smith Den and Lake Skenonto Loop

11.7 km

410 m

Moderate

Tuxedo Park - Tom Jones Mountain - Lake Skenonto

17.6 km

570 m

Hard

Kakiat Trail

29.1 km

1,010 m

Hard

Dutch Doctor Shelter Loop

17.3 km

670 m

Hard

Blue Disc and Ramapo Dunderberg Loop

10.1 km

250 m

Moderate

Ramapo Dunderberg and Triangle Trail Loop

13.5 km

340 m

Moderate

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1.

Tuxedo-Mount Ivy to Triangle Loop

13.4km

03:57

380m

390m

The Tuxedo-Mount Ivy to Triangle Loop offers a diverse and engaging hiking experience through the southern reaches of Harriman State Park. You'll navigate varied terrain, from rocky paths to potentially smoother old road sections, with highlights like the scenic viewpoints near Claudius Smith Den and tranquil breaks by Lake Skenonto. This moderate 8.3-mile (13.4 km) hike involves 1263 feet (385 metres) of elevation gain and typically takes around 3 hours and 57 minutes, making it a rewarding option for those seeking a substantial day out.

Planning your visit is straightforward, with the trailhead providing a good starting point for exploring this part of Harriman State Park. While specific permits aren't usually required, it's always a good idea to check for any local advisories before you go. Parking can fill up quickly on busy days, so an early start is recommended to ensure a smooth beginning to your adventure.

This loop is a clever combination of several trails, including the Tuxedo-Mount Ivy and Triangle Trails, offering a comprehensive tour of the area. It's known for its peaceful, less-visited sections, providing a sense of solitude often hard to find in popular parks. You can even take a short side trip to the Dutch Doctor shelter, adding another point of interest to your journey.

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2.

Ramapo Dunderberg and Triangle Trail Loop

20.1km

06:04

700m

500m

The Ramapo Dunderberg and Triangle Trail Loop offers a challenging and scenic journey through Harriman State Park. You'll navigate rugged terrain, including numerous rock scrambles, and be treated to diverse scenery with beautiful views from Parker Cabin Mountain and overlooks of Lake Skenonto. This difficult 12.5-mile (20.1 km) hike involves 2281 feet (695 metres) of elevation gain and typically takes around 6 hours and 3 minutes, making it a rewarding experience for seasoned hikers.

Planning your visit is straightforward, especially if you're using public transport. The trailhead is conveniently located within a 15-minute walk from the Tuxedo Park train station, a popular option for day-trippers from the New York City area. Ensure you wear proper footwear with good grip for the varied terrain and stream crossings, and consider starting early to make the most of the daylight.

This loop is notable for its distinct "wilderness" feel, a rare find so close to a major metropolitan area. Parts of the Ramapo Dunderberg Trail date back to 1920, adding a touch of history to your adventure. The integration of rock scrambles is often highlighted as one of its most enjoyable and interesting features, setting it apart from other trails in the region.

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3.

Claudius Smith's Den Short Loop

6.92km

02:07

240m

230m

The Claudius Smith's Den Short Loop is a moderate hiking trail that packs a punch with its varied terrain and historical intrigue. You'll navigate rocky paths and uphill sections through dense tree canopies, eventually reaching the impressive Claudius Smith's Den. From the den, you're treated to expansive views of the Ramapo Mountains, a perfect reward for your efforts on this 4.3-mile (6.9 km) journey.

This loop is a great option for a half-day outing, typically taking around 2 hours and 7 minutes to complete with 803 feet (245 metres) of elevation gain. As it's located within Harriman State Park, it's always a good idea to check for any specific park guidelines or parking information before heading out. The trail is well-suited for hikers who enjoy a mix of physical challenge and scenic payoffs.

What truly sets this trail apart is its connection to American Revolutionary War history. Claudius Smith's Den, a massive rock outcrop with a cave, was reputedly the hideout of a notorious outlaw. This natural formation, created by freeze-thaw cycles over 12,000 years, offers a tangible link to the past, making your hike more than just a walk in the woods; it's a step back in time.

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4.

Ramapo-Dunderberg Trail to Tom Jones Shelter

6.93km

02:10

340m

90m

The Ramapo-Dunderberg Trail to Tom Jones Shelter offers a taste of Harriman State Park's rugged beauty, leading you through varied terrain to a rewarding viewpoint. Expect a journey over rocks and roots, with sections of steep climbing that open up to expansive vistas. From the Tom Jones Shelter, you'll be treated to great views of the valley and Lake Sebago, especially striking when the leaves are off the trees, revealing the park's glacially-scoured bedrock and scattered glacial erratics.

This moderate 4.3-mile (6.9 km) hike, with 1122 feet (342 metres) of elevation gain, can be completed in about 2 hours and 9 minutes, making it a solid option for a half-day adventure. The trail is easily accessible from Route 106, with parking available, though it's always wise to arrive early on busy days. Consider visiting in the fall for the most vibrant scenery, but be prepared for potentially tricky footing on the rocky sections.

The Ramapo-Dunderberg Trail is part of a much larger network, known for traversing diverse landscapes across Harriman State Park. The Tom Jones Shelter itself is a notable feature, a lean-to with a fire ring, making it a popular spot for a break or even an overnight stay. This route provides a challenging yet rewarding experience, showcasing the park's natural features and offering a sense of solitude away from more crowded areas.

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5.

Claudius Smith Den and Lake Skenonto Loop

11.7km

03:30

410m

280m

The Claudius Smith Den and Lake Skenonto Loop offers a journey through Harriman State Park's varied landscapes, from shaded woodlands to rocky outcrops. You'll encounter the historic Claudius Smith Den, a large rock overhang that once served as a hideout, and enjoy picturesque views of Lake Skenonto. The trail also features unique natural formations like the Elbow Brush and a rock dam across Black Ash Swamp, making for a constantly engaging experience.

This moderate 7.3-mile (11.7 km) hike involves a significant 1348 feet (411 metres) of elevation gain, typically taking around 3 hours and 29 minutes to complete. Sturdy hiking boots are a must for the varied terrain, which includes steep climbs and rocky sections. Plan to arrive early at the trailhead, especially on busy days, to ensure parking and allow ample time to enjoy the route.

Beyond the natural beauty, this trail is steeped in local history, with Claudius Smith's Den offering a tangible link to the Revolutionary War era. The route provides numerous viewpoints with panoramic vistas of the Ramapo Mountains and surrounding parkland, making it a popular option for those seeking both a physical challenge and scenic rewards in Orange County, New York.

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6.

Tuxedo Park - Tom Jones Mountain - Lake Skenonto

17.6km

05:20

570m

520m

Embark on a challenging yet incredibly rewarding journey through Harriman State Park with the Tuxedo Park - Tom Jones Mountain - Lake Skenonto hike. This difficult route spans 10.9 miles (17.6 km) and involves a significant 1878 feet (572 metres) of elevation gain, typically requiring about 5 hours and 19 minutes to complete. You'll navigate varied terrain, from initial rock steps and carriage trails to the steep, rocky ascent of Tom Jones Mountain, culminating in open summits that offer breathtaking panoramic views of Lake Skenonto and other distant lakes. The experience is a continuous unfolding of natural beauty, especially vibrant during the fall season. This trail is perfect for hikers who enjoy a strenuous workout paired with diverse scenery.

Planning your visit is straightforward, with the trailhead located near Tuxedo, NY, and accessible via public transportation from New York City. While Lake Skenonto provides a picturesque spot for a break, be aware that swimming is prohibited and can result in tickets. To ensure a smooth start, especially on busy days, aim to arrive early to secure parking. This hike is best enjoyed when you have ample daylight and are prepared for a full day on the trails.

This route is a prime example of the extensive and beautiful hiking opportunities within Harriman State Park, a favorite among local hikers for its natural beauty and challenging trails. The area is rich in water features, with numerous streams and small waterfalls encountered along the way, adding to the serene atmosphere. Tom Jones Mountain itself is a notable landmark, often serving as the highest point on various loops and home to a popular shelter, offering excellent views that make the climb worthwhile.

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7.

Kakiat Trail

29.1km

08:46

1,010m

810m

The Kakiat Trail offers a diverse and often challenging hiking experience, weaving through Harriman State Park and Kakiat County Park. You'll navigate everything from flat wetlands to steep mountainsides, with rocky paths and opportunities for boulder hopping. Expect varied tree species, including White Pine and Hemlock, and enjoy scenic views that can stretch to the Manhattan skyline from higher points, making it a rewarding journey for those who appreciate rugged natural beauty.

Planning your visit to the Kakiat Trail requires some foresight, especially for the full 18.1-mile (29.1 km) traverse, which typically needs a shuttle car due to its point-to-point nature. If you're looking for Kakiat Trail loop options, you can combine it with other marked trails, particularly when starting from Kakiat Park. Be prepared for wet sections, especially near the Mahwah River, and note that trail markers can thin out deeper into the woods, so bring a map or GPS.

This difficult route, with 3307 feet (1008 metres) of elevation gain and an estimated duration of 8 hours and 46 minutes, serves as a key artery through the southern part of Harriman State Park. Beyond its natural features, the trail also offers glimpses into history with elements like the Blauvelt Mill Ruins. Wildlife, including snakes and ticks, are common, so stay observant and take appropriate precautions.

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8.

Dutch Doctor Shelter Loop

17.3km

05:22

670m

540m

The Dutch Doctor Shelter Loop in Harriman State Park offers a truly diverse and often challenging hiking experience. You'll traverse rocky inclines and descents, winding through dense forests and past flowing brooks, all while enjoying expansive views of the Ramapo Mountains from various points like Diamond Mountain Summit. This difficult 10.8-mile (17.3 km) route involves 2186 feet (666 metres) of elevation gain, making it a substantial outing that typically takes about 5 hours and 22 minutes to complete.

Planning your visit means preparing for a full day on the trail. Sturdy hiking boots are essential for the uneven and rocky terrain. While there are natural water sources along the way, carrying sufficient water is always recommended. Arriving early, especially on busy days, will help ensure you find parking at the trailhead and give you plenty of daylight to enjoy the entire loop.

One of the most notable features of this loop is the Dutch Doctor Shelter itself, a historic stone structure built in 1935 that provides a unique resting spot or even an overnight camping option. You'll also encounter Claudius Smith's Den, a fascinating rock formation with local lore. The trail's combination of challenging climbs, varied scenery, and historical landmarks makes it a comprehensive and memorable hike in the region.

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9.

Blue Disc and Ramapo Dunderberg Loop

10.1km

02:55

250m

250m

The Blue Disc and Ramapo Dunderberg Loop offers a diverse hiking experience through Harriman State Park, guiding you over varied terrain from rocky inclines to old, eroded roads. You'll navigate the

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10.

Ramapo Dunderberg and Triangle Trail Loop

13.5km

03:55

340m

340m

The Ramapo Dunderberg and Triangle Trail Loop offers a true wilderness experience right in Harriman State Park, combining sections of two historic trails. You'll navigate through diverse terrain, including numerous rock scrambles and stream crossings, with rewarding views from peaks like Black Ash Mountain and glimpses of scenic lakes. This moderate 8.4-mile (13.5 km) hiking route, with its 1119 feet (341 metres) of elevation gain, provides a solid workout that typically takes around 3 hours and 54 minutes.

Planning your trip is straightforward, as the trailhead is conveniently located within a 15-minute walk of the Tuxedo train station, making it an excellent option for those relying on public transport. While it's a popular trail, it generally feels less crowded than some of its regional counterparts, offering a more peaceful experience. Be sure to wear proper footwear with good grip to handle the rocky sections, and consider bringing a physical map for navigation.

This loop is a fantastic way to explore the rich history of Harriman State Park's trail system, with parts of the Ramapo Dunderberg Trail dating back to 1920 and the Triangle Trail to 1939. The varied landscape, from dense forests to open viewpoints, provides a dynamic hiking experience. Keep an eye out for local wildlife, including black bears, and enjoy a challenging day hike that feels a world away from city life.

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Tips from the Community

Joseph
June 23, 2022, Claudius Smith's Den

Nice view of the surrounding area from the top. There are several options to climb up and around the rocks for different skill levels.

0

0

This is one of the park's nine stone lean-tos. A nice spot to spend the night at!

0

0

The top of Parker Cabin Mountain offers good views of the surrounding hills and of Lake Sebago.

0

0

Claudius Smith was a thief who is known to have used these caves as a hideout during the Revolutionary War. From the top of the cave, you get a nice view of the park and surrounding hills.

1

0

This is one of the park's most beautiful lean-to. It sits on a grassy area and holds two interior fireplaces. You'll also find a fire ring, but no water.

2

0

Frequently Asked Questions

How many hiking trails are available around Tuxedo Park?

There are over 100 hiking routes around Tuxedo Park, offering a wide range of options for different skill levels. You'll find everything from easy lakeside strolls to more challenging climbs through the region's dense woodlands and rolling hills.

Are there easy hiking trails suitable for beginners or families?

Yes, Tuxedo Park offers around 30 easy hiking trails. A popular choice for a gentle walk with scenic views is the Sterling Lake loop — Sterling Forest State Park, which circles Sterling Lake and features gentle gradients.

What kind of natural features or landmarks can I expect to see on the trails?

The trails around Tuxedo Park lead through diverse landscapes, including dense forests, rocky outcrops, and numerous lakes. You might encounter interesting natural monuments like the Lemon Squeezer, reach summits such as Jackie Jones Mountain, or discover the beautiful Fitzgerald Falls.

Are there any challenging hikes for experienced hikers?

Yes, for those seeking a more strenuous experience, there are 9 difficult trails in the area. Many moderate routes also offer significant elevation changes. For example, the Ramapo Torne Loop — Harriman State Park is a moderate trail with over 300 meters of elevation gain, providing a good workout.

What do other hikers say about the trails in Tuxedo Park?

The hiking routes around Tuxedo Park are highly regarded by the komoot community, with an average rating of 4.8 stars from over 80 reviews. Hikers often praise the varied terrain, the beauty of the dense forests, and the peaceful atmosphere of the state parks.

Are there any circular hiking routes available?

Yes, many trails around Tuxedo Park are designed as loops, allowing you to start and end at the same point. The Diamond Mountain loop via the Stony Brook Trail — Harriman State Park is a popular moderate circular route exploring varied forest terrain.

Can I find shelters or huts along the hiking paths?

Yes, within the larger park areas surrounding Tuxedo Park, you can find several shelters and huts. Notable options include the Stone Memorial Lean-to Shelter and the Bald Rocks Shelter, which can be useful for longer excursions.

Are there any historical sites to explore while hiking?

Beyond natural beauty, you can discover historical points of interest. For example, the Pine Swamp Mine is an interesting historical site that can be incorporated into your hiking adventure.

What are some good options for moderate hikes in the area?

Tuxedo Park has a large selection of moderate hikes, with around 80 routes falling into this category. Besides the popular Diamond Mountain loop, the Claudius Smith's Den loop — Harriman State Park is another excellent moderate option, leading through rugged landscapes.

Are there any trails that offer great viewpoints?

Many trails in the Tuxedo Park area ascend to low peaks and rocky outcrops, providing scenic viewpoints over the surrounding forests and lakes. While specific named viewpoints are not always marked, the varied terrain ensures many opportunities for panoramic vistas, especially on routes with significant elevation gain like the Daters Mountain Loop – Harriman State Park.

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