Let me show you some of the best hikes near Woodstock NY which in my opinion is one of the most awesome towns to check out in the upstate area. On top of that, you’ll find trails all over the area with others leading deeper into the Catskills.
Best hikes near Woodstock NY:
- Overlook Mountain Trail
- Ashokan Rail Trail
- Comeau Property
- Huckleberry Point
- Sloan Gorge Loop
Let me cover each one and help you understand which is the best option for you to check out.
Overlook Mountain Trail:
- Length: 4-5 miles
- Elevation: 500 feet
- Difficulty: Moderate
- Highlights: Ruins, Fire Tower, beautiful views of the Hudson and Catskills
The Overlook Mountain Trail was the first hike I ever checked out near Woodstock. It blends together natural beauty and historical intrigue. The trail is known for its steady uphill path leading to the ruins of the Overlook Mountain House, a historic hotel now known as the Ruins. That walk up to the ruins is pretty boring but it becomes an amazing experience after.
As you ascend, you can explore these remnants before reaching the summit where a fire tower provides expansive views of the Catskill Mountains and Hudson Valley. This trail is particularly popular for sunrise hikes due to the stunning vistas it offers. It’s accessible year-round but spring and fall are my personal recommendations.
Ashokan Rail Trail:
- Length: 11-12 miles
- Elevation: 200 feet
- Difficulty: Moderate
- Highlights: Easy walk/hike, great bike trail, good sealevel views
The Ashokan Rail Trail offers a serene and accessible outdoor experience near Woodstock, NY and unlike typical hiking trails, the Ashokan Rail Trail is wide, flat, and mostly paved, making it ideal for walkers, cyclists, and runners of all abilities.
The trail is mostly famous for its breathtaking views of the Catskill Mountains and the expansive reservoir. If you can’t do the full 11 mile walk the good news is that throughout the area, there’s multiple parking lots and access points making the trail easily reachable for short visits or longer excursions.
Comeau Property trail:
- Length: 1 mile
- Elevation: 100 feet
- Difficulty: Easy
- Highlights: The closest trail within Woodstock with great views
The Comeau Property trail is the closest trail to Woodstock. In fact it’s literally in it and offers a tranquil escape away from it with an easy and short loop.
I recommend this trail for those looking for a quick and relaxing walk, as it meanders alongside a beautiful stream and through lush woodland (depending on when you visit it). This is the most simple, yet beautiful trail on the list.
Huckleberry Point:
- Length: 4-5 miles
- Elevation: 600
- Difficulty: Moderate
- Highlights:
The Huckleberry Point trail is one of the most adventurous hikes you’ll find in Woodstock NY. It’s a rewarding trail overall and provides stunning views from the cliff edge you’ll walk on when you reach the summit area.
While it is moderate, most beginners can probably do it too and I strongly recommend it. The trail does include some steep sections that make for fun climbs, but these efforts are rewarded with breathtaking views of the surrounding Catskill Mountains and valleys below. At the endpoint (Huckleberry Point) is a scenic overlook that provides a perfect photogenic spot and a peaceful spot to enjoy a picnic while taking in the natural beauty.
Sloan Gorge Loop:
- Length: 1.5 miles
- Elevation: 400 feet
- Difficulty: Easy
- Highlights: Great hike within Woodstock to see the signs and some quiet areas near it
The Sloan Gorge Loop near offers a unique hiking experience with a blend of natural beauty and geological interest. This loop trail is relatively short, making it a great option for a quick hike that still offers plenty of sights. You can probably do this and another short trail from the above list to make a day trip out of it.
The Sloan Gorge Loop features interesting rock formations and a small waterfall, providing an awesome backdrop for any nature lover in my opinion. The path through Sloan Gorge winds through a beautifully wooded area, so if you hike here during warmer seasons, you’ll have shade and water to cool down as you progress throughout. The trail is accessible to most hikers including beginners, is usually very peaceful one of the best near Woodstock.
When to do these hikes:
- Early mornings (less crowds)
- Weekdays (also less crowds)
- Spring or fall (chilly weather mostly and during fall is when these hikes are 10x better in views)
If you do come here on a weekend or during summer just know you’ll likely have tons of crowds on the trails with you. If you don’t mind that (or possibly looking for parking) then you can really come here anytime, but the suggestions above will help you get the most out of the hikes when you visit. And of course afterwards, be sure to visit a restaurant in Woodstock to finish up!
Other recommendations:
- No matter when you go, please wear overall clothing because it’ll protect you from ticks which are some of the most dangerous animals in Upstate NY.
- I wouldn’t worry too much about bears but you should go with friends if you can, it’ll be more fun that way.