9 Beautiful Hikes in Woodstock, NY: All Levels!
If you're visiting Woodstock and are looking for a great hike with views or a waterfall or even a historic quarry then you're in luck! Discover 9 different hikes and trails in Woodstock fit for every level.
There's so much to do in Woodstock, NY and lots to see but to me the hikes here are at the top of the list!
There’s a certain magic to hiking in Woodstock, where the creative energy of town blends with the quiet beauty of the Catskill Mountains.
Woodstock may be famous for its artsy downtown and creative spirit, but step just beyond Tinker Street and you’ll find some of the most peaceful and rewarding hiking trails in the Catskills.
From sweeping fire tower views from Overlook Mountain, to family-friendly trails through meadows at Thorne Preserve, and one of the tallest waterfalls in NY at Kaaterskill Falls - there's tons to choose from around Woodstock.
Living next door in Connecticut, this area keeps me coming back to visit every season!
So let's get to it and help you find your next favorite trail in Woodstock, NY!
9 Best Hikes In & Near Woodstock, New York
1. Overlook Mountain
- 🥾Miles & Difficulty: 4.6 miles, Moderate
- 📈Elevation Gain: 1,397 ft
- 🚙Parking: Click to navigate here: 42.0711, -74.1227 Small parking lot on MacDaniel Rd
- 🌟Highlights: 360-degree views from tower plus ruins from Overlook Mountain House
Overlook Mountain is located minutes from downtown and stands as one of Woodstock’s most iconic hiking destinations, offering a blend of natural beauty and historical intrigue. We hiked here in the winter which was perfect as we only saw a few other people on a Saturday.
It gets very busy here on weekends in summer and fall given it's location, tower, and old hotel at the top. And while it's a great workout, you'll be walking on wide and well-maintained gravel path which makes it accessible to hikers of various skill levels.
One of the standout features along the Overlook Mountain trail is the incredible ruins of the Overlook Mountain House, a once-thriving abandoned hotel that adds a touch of history to your hike.
And then the final highlight awaits at the summit, where the Overlook Mountain Fire Tower stands tall. Climb to the top of this fire tower rewards you with breathtaking 360-degree beautiful views of the Hudson Valley and surrounding mountains, making every step worth the effort.
2. Ashokan Quarry
- 🥾Miles & Difficulty: 1.9 miles, Easy
- 📈Elevation Gain: 216 ft
- 🚙Parking: Navigate here: 41.93516, -74.22887 parking lot off State Hwy 28A
- 🌟Highlights: Views facing west
The Ashokan Quarry Trail offers a unique blend of natural beauty and historical significance. Hiking along the trail reveals various remnants from the construction of the Ashokan Reservoir, including historical equipment and a rail car loading area.
We hiked here at sunrise time and though the view faces west it was fun to see the sunlight hit the mountains and light them as it rose!☀️
It's also a trail that doesn't require a lot of though as you walk - just a straightforward, non-technical path which we appreciated so early in the morning.
3. Onteora Lake Loop
- 🥾Miles & Difficulty: 3.2 miles, Easy
- 📈Elevation Gain: 272 ft
- 🚙Parking: Navigate here: 41.98407, -74.0828 Lot along Route 28
- 🌟Highlights: Peaceful woods loop arouond 2 different lakes
The Onteora Lake Loop is a moderately challenging trail that takes you along two different lakes; Onteora Lake and then Pickerel Pond.
Shortly after starting on the path you'll arrive at Onteora Lake where the dogs enjoyed splashing around and sips of water. You continue walking along the western side of Onteora Lake then head into the woods.
At 0.6 miles in the loop portion begins and from here you'll walk up along a ridge where you can see Pickerel Pond and you'll meet its shore briefly before heading back in the woods.
This 3.2-mile loop is long enough to tire everyone out so you could finish exploring the town of Woodstock relaxed while the dogs nap! 🙂
4. Snake Rocks Preserve
- 🥾Miles & Difficulty: 1.5 miles, Easy
- 📈Elevation Gain: 242 ft
- 🚙Parking: Navigate here: 42.02459, -74.14807 pull-off spots along Yerry Hill Road
- 🌟Highlights: quarry pond
The Snake Rocks Preserve, right outstide of downtown, is another must-visit spot for adventurers visiting Woodstock, NY.
This preserve is located known for its striking quarry pond. The historic bluestone quarry, dating back to the late 1800s, offers a glimpse into the region’s industrial past.
This is a nice short hike in Woodstock but you may be a little confused on the parking situation. There is a small pull-off along Yerry Hill Rd. From here you'll walk north along Yerry Hill for a short time before turning left to go up Nordic Drive where you'll walk uphill for about 0.25 miles before turning left into the woods following the Snake Rock Preserve sign. 🙂
Trekking through the Snake Rocks Preserve offers views from the top of quarry tailings, providing a unique vantage point of the surrounding landscape.
The combination of historical significance and fun quarry views makes this hike a memorable adventure.
5. Thorn Preserve Loop
- 🥾Miles & Difficulty: 1.2 miles, Easy
- 📈Elevation Gain: 19 ft
- 🚙Parking: Navigate here: 42.02001, -74.07441 Small lot along John Joy Rd.
- 🌟Highlights: Flat and wide path through scenic open meadow with views of the mountains
Thorn Preserve, minutes from downtown Woodstock, offers a picturesque loop hike that spans 60 acres of diverse ecosystems, including grasslands, ponds, and forests.
The well-maintained wide path walking paths are easily accessible from John Joy Road, making it a convenient spot for an easy stroll right in Woodstock.
We did a quick walk here right before dinner time as the sun was setting. And since it's mainly flat it was the perfect pre-dinner stroll in our jeans and boots. The only downside is dogs are not allowed at Thorn Preserve. :/
Thorne Preserve offers stunning views of Overlook Mountain, providing a beautiful backdrop for your hike. It's a delightful escape into nature and offers an easy, peaceful place to walk for people of all ages.
6. Kaaterskill Falls
- 🥾Miles & Difficulty: trails ranging from 1.7 miles to up to 10 miles!
- 📈Elevation Gain: depends on the trail you choose
- 🌟Highlights: Kaaterskill Falls with two cascades totaling 260 feet in height
Though Kaaterskill Falls is a 40 minute drive from Woodstock, I had to include it as it's one of the tallest waterfalls in New York. And if you're visiting Woodstock NY for a weekend this may be a good option for a morning day trip!
Kaaterskill Falls features a remarkable two-tiered drop with a total height of about 260 feet. There are several trails you can take to the falls. Here is a full list of the trails to Kaaterskill.
The main access trail is the shortest and easiest and begins at the Laurel House Road parking area, leading to an observation deck with stunning views of the falls.
The Escarpment Trail, with its steep stone steps, offers a more rigorous hike for those seeking a challenge. Kaaterskill Falls is renowned for its breathtaking views and stands as one of the tallest waterfalls in New York.
7. Sloan Gorge Loop
- 🥾Miles & Difficulty: 1.3 miles, Easy but rocky (wear sturdy shoes or boots)
- 📈Elevation Gain: 72 ft
- 🚙Parking: Navigate here: 42.07059, -74.06873 Lot along Stoll Rd
- 🌟Highlights: rock formationsalong a gorge
The Sloan Gorge Loop offers a relaxed and short family-friendly adventure right in Woodstock. Along the trail you’ll encounter a fascinating bluestone quarry and a narrow rock split, both of which add to the preserve’s charm.
I haven't tried this one yet but its proximity to Woodstock and easy of trail might make it the perfect hike!
8. Comeau Property
- 🥾Miles & Difficulty: 0.8 miles, Easy
- 📈Elevation Gain: 82 ft
- 🚙Parking: Navigate here: 42.03804, -74.12601 Lot along 108/Mountain Rd near Barnes Visitor's Center and The Lodge at Spruce Peak
- 🌟Highlights: flat path along Saw Kill River
The Comeau Property is a serene haven for those looking to escape into nature without venturing far from Woodstock. Covering 36 acres, this property features a one-mile circular hiking trail that offers a gentle elevation gain of 82 feet.
The well-maintained walking path meanders through scenic woodlands, and is another option if you'll looking for a leisurely stroll.
The Comeau Property features diverse wildlife and natural elements like a stream, enhancing the trail’s tranquility. The trail is designed to be easy and typically takes between 30 minutes to one hour to complete, making it perfect for a quick escape into nature.
9. Ashokan Paved Rail Trail
- 🥾Miles & Difficulty: up to 11.5 miles long, flat
- 🌟Highlights: Once above tree line, you're rewarded with amazing views and a tricky climb up to the Chin from the Adams Apple and down the Forehead!
The Ashokan Rail Trail is a fantastic option for those who want a walk along a paved trail which is also great for biking or pushing a stroller.
Accessible from three main trailheads, the Ashokan Rail Trail runs all along the Ashokan Reservoir with scenic views along the way. The trail is open year-round from sunrise to sunset. Its year-round accessibility means you can enjoy the trail’s beauty in any season, whether it’s the vibrant colors of fall or the serene snowscapes of winter.
Blending natural beauty and accessibility, the Ashokan Rail Trail is one of the most accessible trails to visit for exploring Woodstock, NY. Whether you’re planning a hike, a bike ride, or a casual walk, this perfect blend track trail starts offers something for everyone.
Summary
Woodstock, NY, offers a diverse array of hiking trails that cater to all kinds of outdoor enthusiasts. From the challenging ascent of Overlook Mountain with its historical ruins and stunning fire tower views, to the family-friendly paths of Sloan Gorge Preserve, there’s a trail for every hiker here!
The serene beauty of Comeau Property and the long Onteora Lake Loop provide unique experiences that highlight the natural and historical richness of the area.
Whether you’re looking for a leisurely stroll or a heart-pumping adventure, Woodstock delivers. The Ashokan Rail Trail, with its accessible and scenic route, and the iconic Kaaterskill Falls, with its breathtaking waterfall, ensure that your hiking experience is both memorable and rewarding.
So pack your gear, choose your trail, and embark on an unforgettable journey through the beautiful landscapes of Woodstock, NY!
I hope you found your next favorite hike in Woodstock on this list! 🙂 Feel free to post any questions or comments below, I'd love to hear from you! 📨
Frequently Asked Questions
What is the best time to hike Overlook Mountain?
The best time to hike Overlook Mountain is early in the morning when it's less crowded.
Are the trails at Sloan Gorge Preserve suitable for families?
Absolutely, the trails at Sloan Gorge Preserve are family-friendly with gentle terrain and little elevation change, so they’re perfect for enjoying a day out together.
Is the Ashokan Rail Trail accessible year-round?
Absolutely! The Ashokan Rail Trail is open year-round from sunrise to sunset, so you can enjoy it no matter the season.
Can I bring my dog to the Comeau Property trail?
Absolutely, you can bring your dog to the Comeau Property trail since it’s pet-friendly. Just make sure to keep your pup on a leash and clean up after them!
What makes Kaaterskill Falls a unique hiking destination?
Kaaterskill Falls stands out because it’s one of New York's tallest waterfalls at 260 feet, and the hike gives you some breathtaking views along with a perfect mix of challenge!
