The best walks and hikes around Woodstock
4.7
(47)
681
hikers
32
hikes
Hiking around Woodstock, New York, is characterized by the rugged beauty of the Catskill Mountains. The region features a blend of challenging ascents and leisurely trails, with landscapes including dramatic rocky gorges, bluestone cliffs, and dense forests. Hikers can explore diverse ecosystems, from grasslands and ponds to old-growth woodlands, offering varied terrain for outdoor activities.
Best hiking trails around Woodstock
- The most popular hiking route is Overlook Spur Trail, a 4.6 miles (7.4 km) trail that takes 2 hours 30 minutes to complete. This moderate route leads to impressive hotel ruins and a fire tower with panoramic views.
- Another top favourite among local hikers is Mink Hollow Trail to Twin Mountain, a difficult 4.9 miles (8.0 km) path. This trail offers significant elevation gain through the Indian Head Wilderness.
- Local hikers also love the Onteora Lake Loop Trail, a 3.8 miles (6.1 km) trail leading through varied forest terrain, often completed in about 1 hour 35 minutes.
- Hiking around Woodstock is defined by the Catskill Mountains, dramatic rocky gorges, and bluestone cliffs. The network offers options for different ability levels, from easy lakeside loops to challenging mountain ascents.
- The routes in Woodstock are highly rated by the komoot community with an average score of 4.7 stars from more than 30 reviews. More than 600 hikers have used komoot to explore Woodstock's varied terrain.
Last updated: July 8, 2026
5.0
(5)
54
hikers
5.63km
01:54
420m
40m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
1
hikers
7.96km
04:00
900m
270m
Hard hike. Good fitness required. Sure-footedness, sturdy shoes and alpine experience required.
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1.35km
00:22
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.5
(12)
256
hikers
7.41km
02:31
400m
400m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5.0
(3)
24
hikers
6.06km
01:35
40m
40m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Tips from the Community
From the fire tower, the 360° view is impressive. The Ashokan Reservoir, the Hudson Valley and the small Echo Lake are visible from the top of the tower. Access is closed during the winter months. Luckily during our visit the ranger had come to open the tower since the weather was nice and it was the holidays. From the Overlook point, however, the view is limited by the trees.
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Trail hike around a lake. Be sure you have GPS with you could get lost. Trail not marked except by foot path.
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The Onteora Lake Trail forms a loop on the eastern banks of the reservoir and follows the western banks to the main parking area. The trail is mostly wide singletrack consisting of dirt and grass through wetland and forest environments.
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There are a handful of different trails in Bluestone Wild Forest where Onteora Lake is located. The lake is pretty big and has paths on both sides. This trail system can get busy since it's open to hikers, runners, and mountain bikers, so be sure to stay aware of other users.
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The Onteora Lake Trail forms a loop on the eastern banks of the reservoir and follows the western banks to the main parking area. The trail is mostly wide singletrack consisting of dirt and grass through wetland and forest environments.
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This viewpoint will certainly reward you for climbing to the top of Overlook Mountain! This is the most southerly peak of the Catskill Escarpment, with a height of over 900m. From here you'll have views over the Hudson River Valley and further afield.
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This fire tower is open to the public to walk up and take in the amazing panoramic views, if you don't mind the height (it is 60-feet tall). From the top you'll be rewarded with views over the Hudson River Valley and further afield, including the Ashokan Reservoir. The fire tower was built in 1950 and is one of 5 remaining fire towers in the Catskill Park.
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Onteora Lake is a small lake which is great for watersports. This is a lovely tranquil setting, great for a rest stop and a picnic. Originally, the lake was created by damming the Esopus Creek in the early 1900s. There are multiple mountain biking and hiking trails here, of varying levels of difficulty.
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Frequently Asked Questions
How many hiking trails are there in Woodstock, NY?
The Woodstock area offers over 20 hiking trails, catering to various skill levels. You'll find a mix of easy, moderate, and challenging routes through the Catskill Mountains.
What are some easy hiking options around Woodstock, NY?
For an easier experience, consider the Onteora Lake Trail loop, which is 3.8 miles (6.1 km) and leads through varied forest terrain. The Ashokan Rail Trail also provides a wide, flat, and accessible path ideal for leisurely walks.
Are there any challenging hikes in the Woodstock, NY area?
Yes, for a more strenuous adventure, the Twin Mountain & Indian Head Mountain Loop is a difficult 7.8 miles (12.6 km) path with significant elevation gain through the Indian Head Wilderness. Another challenging option is the Twin Mountain Loop.
Can I find circular hiking routes near Woodstock, NY?
Several trails offer circular routes, allowing you to start and end at the same point. The Onteora Lake Trail loop is a great example, as is the Twin Mountain & Indian Head Mountain Loop.
What natural features can I expect to see on hikes in Woodstock, NY?
Hiking in Woodstock, NY, immerses you in the rugged beauty of the Catskill Mountains. You'll encounter dramatic rocky gorges, imposing bluestone cliffs, and dense forests. Diverse ecosystems, including grasslands, ponds, and old-growth woodlands, are common sights.
Are there any historical landmarks or unique viewpoints along the trails?
Absolutely. The Overlook Mountain trail leads to impressive hotel ruins and a 60-foot fire tower, offering panoramic views. You can also visit the Overlook Mountain Fire Tower itself for stunning vistas. The View of Ashokan Reservoir and Catskill Mountains is another notable viewpoint.
Is Woodstock, NY a good place for family-friendly hikes?
Yes, Woodstock offers options suitable for families. The Ashokan Rail Trail is particularly good, being wide, flat, and accessible. The Comeau Property also offers a short, easy loop ideal for a leisurely family walk.
Are dogs allowed on hiking trails in Woodstock, NY?
Many trails in the Woodstock area are dog-friendly, but it's always best to check specific trail regulations before heading out. For example, the Ottauquechee River Trail (in Woodstock, VT, but similar policies often apply in the region) is known to be dog-friendly. The Thorn Preserve also welcomes dogs on its paths.
Where can I park when hiking in Woodstock, NY?
Parking availability varies by trailhead. For popular spots like Overlook Mountain, designated parking areas are available, though they can fill up quickly during peak times. The Ashokan Rail Trail — Woodstock Dike Trailhead also has parking facilities. It's advisable to arrive early, especially on weekends.
What is the best time of year to go hiking in Woodstock, NY?
Spring and fall are generally considered the best times for hiking in Woodstock, NY. Spring brings blooming wildflowers and pleasant temperatures, while fall offers spectacular foliage. Summer can be warm and humid, but trails are still enjoyable, and winter hiking is possible for experienced individuals with proper gear.
Are there any less crowded hiking trails in Woodstock, NY?
While popular trails like Overlook Mountain can get busy, exploring lesser-known paths or visiting during off-peak hours can lead to a more tranquil experience. The Sloan Gorge Preserve offers a unique, shorter hike that might be less crowded than major mountain trails. The Snake Rocks Preserve also provides a quieter experience through wooded trails.
What do other hikers say about the trails in Woodstock, NY?
The trails in Woodstock are highly rated by the komoot community, with an average score of 4.7 stars from over 30 reviews. Hikers often praise the diverse terrain, from challenging mountain ascents to easy lakeside loops, and the stunning views of the Catskill Mountains.
Are there any waterfalls near Woodstock, NY that I can hike to?
Yes, the region is home to Kaaterskill Falls, a significant natural feature offering various trails ranging from 1.7 to 10 miles in length. This is a popular destination for those seeking impressive waterfalls.
Are there any trails that offer unique geological features like quarries or gorges?
The Sloan Gorge Preserve is known for its dramatic rocky gorge, imposing bluestone cliffs, and a unique rock passage called "The Chimney." Additionally, the Snake Rocks Preserve features wooded trails winding around an abandoned bluestone quarry, providing historical insights into the region's geology.
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