5 Things to Know About The Overlook Mountain Trail in NY

As much as I know about popular hikes in upstate NY, I was surprised to recently discover one called Overlook Mountain Trail that is not only super popular, but for good reasons: It’s stunning in many ways. Having literally completed it yesterday, I want to share 5 things you need to know before you do it too.

Quick info about the Overlook Mountain in Woodstock NY:

• Name: Overlook Mountain Trail.
• Location: Near Woodstock, NY.
• Distance: 4-5 miles (in and out).
• Difficulty: Moderate and difficult at times.
• Dangerous hike? Not really, just don’t do foolish things.
• Pros of the trail: Scenic views of the Hudson, The Catskills, Fire Tower and Ruins.
• Rating: 4.5 out of 5.

In a moment I’ll be covering the most important things to know and expect before you go on this hike, but this overview are just very important things to keep in mind.

5 things to know about the Overlook Mountain hike (summary):

1. The first 1.5 miles is difficult and boring.
2. Make sure to explore the Overlook Mountain House Ruins.
3. Check out the Border Overlook Indian Head spot (scenic views).
4. Hike up to the Fire Tower nearby.
5. Try one or more of the connecting trails at the top.

I’ve included a map with basics for reference on what to expect, but for more context, keep reading because there are parts of this hike you know know about before you go.

Basically, the first 1.5 miles is the boring part, and then it gets really good, but there’s also stuff on the good parts of this hike you should know about prior and that will be covered in a moment as we go through these 5 things

They go in order of what you’ll run into as you progress on this trail hike.

1) Expect the first 1.5 miles of the hike to be difficult (and not very scenic):

This hike begins at Overlook Mountain Trailhead. Nearby you will find a Buddhist temple but the parking lot can hold up to 30 cars. Anyway, once you cross the trailhead sign, it’s literally uphill for 1.5 miles and that can be really difficult for some people.

Adding a bit more salt to that fact, you should also not expect awesome views for this portion of the hike. There will be some clearing spots where you will be able to see the Catskill Mountains in the distance, but for the most part, nothing else of note.

Fortunately, this part of the hike is the only boring and longest part before things get really good, so if you can tough it out for that period, you’ll be fine. Another pro to note is that it’s just 1 road leading up to the top, so you don’t have to worry about getting lost in the woods.

Recommendations for making this part of the hike easier:

1) Use trekking poles. I wish I had bought mine with me (The Trailbuddy trekking poles) as they make the uphill walk here (and downhill when you go back way easier. When I came here, it was after finishing the Labyrinth hike in Mohonk Preserve so we weren’t exactly at a 100%. We also didn’t expect this part of the hike to be so long, and difficult, and went in without trekking poles.

2) Wear decent hiking shoes or trail running shoes. In my personal case, my go to recommendation here is the Salomon Speedcross 5. Just as well, any decent pair of hiking shoes or trail running shoes will make this part of the hike (and any hike in general) way easier on your feet and legs.

2) Be sure to check out the Overlook Mountain house ruins:

I’m a big fan of finding places like this across the Hudson River Valley and this is the most recent one I discovered that is on this trail.

It’s basically 2 large buildings that have been around for over 100 years to my knowledge that you can explore in and out.

The good news is that the ruins are right after you finish the long/boring part of the hike so you will get a major pay off for views (you can’t miss it).

Now if this kind of stuff interests you, I would also recommend checking out similar ruins on a trail called Bull Hill Loop which is located in Hudson Highlands State Park (also very scenic).

My buddy and I took at least 30 minutes to explore this place and while it is amazing, understand that there are a lot of broken areas here (broken glass and other debris lying around too sometimes) that could be dangerous so just exercise caution when exploring it.

But it is overall an amazing place to check out and take pictures in. Surprisingly the day we came here, in spite of it being a super popular trail, we were surprised to see very few people the entire time.

3) Check out the famous overlook afterwards:

It’s called Border Overlook Indian Head, but it’s basically 1/4 miles up the same trail after you pass the ruins.

You will see signs for it, and a short walk from the sign (near the Fire Tower) is where you’ll find it.

My buddy and I were told about this scenic overlook while making our way up Overlook Mountain and we didn’t believe the claims of how good this area was until we saw it for ourselves (the rumors were justified).

You’ll get an incredible view of the Hudson from a distance as well as a large reservoir called Ashokan reservoir. In fact, the body of water you see in the image here is of that particular spot.

There are also hiking trails around it you can check out if that particular stuff interests you. The Hudson River is left of that (from the picture you see).

But this overlook faces the eastern side of the Catskills, and you will really only see the Hudson River Valley from it. The next spot on this list is literally 100 feet away and gives you 360 views of everything and that is:

4) Explore the Overlook Mountain Fire Tower after:

In my opinion, this Fire Tower hike should be done after you check out the scenic spot earlier.

Its one of the best Fire Towers I’ve seen in New York and one of the reasons why is because it’s very tall and you will be able to get incredible views everywhere, including the western side of Overlook Mountain that faces the Catskill Mountains.

Now when my buddy and I went there, the very top access part of the Fire Tower was closed off, but you can still walk up to the near top of it for some nice views all around.

Right on the bottom of it is a fire pit area and 1 picnic table where you can relax, but keep in mind that in many cases, there are high winds in the area (and it can get chilly) so if you want to take a break from the hike (or you’re not a fan of walking up to Fire Towers because you don’t like heights), this is where you can do that.

Now at this point, you will have seen the best parts of the Overlook Mountain hike, but there is one more thing you can do if you have time and interest and that is:

5) Explore more connecting trails by the Overlook Mountain (The Catskills):

As my buddy and I were making our way to the scenic overlook and Fire Tower spot, we saw signs for at least 2-3 different hikes.

There are connecting trails from Overlook Mountain to other incredible hikes in the Catskill Mountains and in this case, the one that jumped out at me is that there is a 6+ mile trail from Overlook Mountain to Prediger Road (north bound), which happens to be the starting point of a very famous hike called Devils Path. There is also Slide Mountain Trail not too far away.

On the way (I checked), you will also see other connecting trails to other cool spots.

The point is, if you enjoy exploring hikes and specifically doing long hikes, then this might be something that is up your alley!

Just as well, there are also other nearby hikes in Woodstock that connect to the Overlook Mountain trail/s that you can check out on maps and use apps like AllTrails for (like the one by the reservoir I mentioned earlier).

But if that doesn’t interest you, all you need to do (if you’re ready to leave) is just head back down the same path to get back to the parking lot. And that will have you complete the Overlook Mountain trail!

More questions about the Overlook Mountain hike:

How tall is Overlook Mountain in Woodstock NY?

The top of Overlook Mountain is a little over 3,100 feet.

Overall the Overlook Mountain trail is very nice for many reasons including:

• It leads to incredible views of the Hudson.
• There’s a fire tower.
• You get to see old buildings (I personally like that).
• There’s the town of Woodstock to also see and eat at after.

This really makes it one of the best hikes near NYC that I have seen and it’s a place I’ll likely check out again and possibly try to see what other trails lead deeper into the Catskills from there.