Hiking The Overlook Mountain Trail – Woodstock NY

Catskill Mountains from top of Overlook Mountain Woodstock NY

Pin This For Later!

Last Updated on September 22, 2021 by Lori

If you love to hike, then hiking in the Catskill Mountains should be on your bucket list!

The Overlook Mountain Trail in Woodstock, NY will lead you on a journey to not only incredible views of up to five states but also a Fire Tower and an abandoned hotel ruin that you won’t see on any other trail.

This post contains affiliate links which means if you click on a link and make a purchase, I will earn a commission at no additional cost to you. Please see our Disclosure Policy for more information.

Why You Should Hike The Overlook Mountain Trail

view from Fire Tower Overlook Mountain
View from Overlook Mountain Fire Tower Woodstock, NY Photo by L. Andrews

When we travel, we look for hikes in the area to explore. What we usually end up finding are amazing waterfalls, fun hiking trails, or an awesome view where you can see for miles.

The Catskill Mountains in New York is one of our very favorite areas to hike. 

Catskill Mountains from top of Overlook Mountain Woodstock NY
Catskill Mountains from the top of Overlook Mountain Woodstock, NY
Photo by: L. Andrews

While we are not advanced hikers, we’ve found many Easy Hikes in the Catskills that also lead to amazing views of the region.

This trip, however, I wanted to try something a little more challenging.

I wanted to hike one of the Five Fire Tower Hikes the Catskills are known for.

Fire Tower on Overlook Mountain Woodstock, NY
Overlook Mountain Fire Tower, Woodstock, NY Photo by: L. Andrews

I had read about the Overlook Mountain Fire Tower and the abandoned Overlook Mountain Hotel ruins at the top.

Overlook Mountain House overgrown ruins
Overlook Mountain Hotel on Overlook Mountain, Woodstock, NY Photo by L. Andrews

The abandoned hotel intrigued me and I decided that we were going to hike to the top of Overlook Mountain when we went on our camping trip to Sleepy Hollow Campgrounds in Phoenicia, NY.

In my research, did I read where it said the mountain hike was a “moderate – hard” trail?


Did I read that the Overlook Mountain Trail rattlesnakes were common?


I just wanted to reach the top of the mountain and climb the Fire Tower.

It was probably a good thing I didn’t read that before we started up the mountain, or I may have backed out.

So, on a beautiful summer day, we set out with Buddy, our Golden Retriever on an outdoor adventure up the mountain.

golden retriever hiking the Overlook Mountain Trail

Where Is Overlook Mountain?

Overlook Mountain Catskills is located in the town of Woodstock, NY. 

To find the trail leading to Overlook Mountain, you will travel through the cute town of Woodstock, and drive up to the trailhead via Meads Mountain Road.

Overlook Mountain Trail Parking

The trailhead parking area is located across from the Tibetan Buddhist Monastery and parking is limited.

Buddhist Monastery at Overlook Mountain Parkling lot

This is very important.  ONLY park in designated parking spaces. 

If you make your own parking spot (as people have been known to do), you will be ticketed.

There is an overflow lot about ¼ mile down the road with a trail connecting to the Overlook Mountain trail.

Catskill Hiking On the Overlook Mountain Trail

Trail To Overlook Mountain

Overlook Mountain has an elevation of 3,140 ft. The trail is a 4.6 mile out and back trail.

The hiking trail also connects to Echo Lake, Devil’s Kitchen Lean-to, and Indian Head Mountain.

I was surprised when we actually started the trail up Overlook Mountain that it was a gravel road and not a trail per se.

Start to Overlook Mountain trail Woodstock NY

The road was once a carriage road to transport guests to the Overlook Mountain House.

The trail itself isn’t difficult, but it climbs steadily up the mountain which may make the hike harder for some.

Also, depending on the month and day of the week, the trail can be busy and you might be waiting on long lines at the top to climb the Fire Tower.

We hiked mid-week during the summer and had no problem finding a parking spot and we did not have to wait to climb the Fire tower.

We saw all ages on the Overlook Mountain hike.

Hikers returning down the mountain would tell us, “You’re halfway there!” or “Just another half hour to the Overlook Mountain House!”

I was determined to make it to the top!

Buddy, our golden loves to take the lead on hikes.  He steadily walked alongside us and kept me going along the way.

While you don’t see the road is steadily climbing, you can feel it – especially if you’re not an avid hiker.

I have to say that we took many breaks along the way – but I kept going.

Soon, my husband called back to me that around the curve ahead was the Overlook Mountain House!

inside Overlook Mountain House
Inside the ruins of Overlook Mountain House, Woodstock, NY Photo by: L. Andrews

I had climbed the 1.6 miles (2,900 ft) to the castle ruins of the Overlook Mountain House.

The first goal of my journey – COMPLETE!

History of The Overlook Mountain House

Overlook Mountain House Woodstock NY
Overlook Mountain House, Overlook Mountain Catskill Mountains. Photo by: L. Andrews

The Overlook Mountain Hotel was the first hotel built on the mountain in 1833. 

At that time, tourism was exploding in the Catskills and the hotel was built to compete with nearby Catskill Mountain House

The hotel opened in 1871 and held 300 guests. It was at a higher elevation than Catskill Mountain House or any other hotels in the area.

Overlook Mountain Hotel Ruins
Overlook Mountain Hotel Woodstock, NY Photo by L. Andrews

Unfortunately, a fire destroyed the hotel in 1875. 

Although the hotel was rebuilt and then reopened, by then they faced fierce competition from neighboring hotels. Plus the challenge of transporting guests up and down the mountain proved to be a problem.

The hotel burned down again in 1923.

An architect was hired to rebuild it for the third time; it never happened and the hotel was left abandoned.

Overlook Mountain House Hotel abandoned

We explored Overlook Mountain House until we were ready to hike the .8 miles to the Fire Tower to reach the top – 3,140 ft.

Trailhead signs on Overlook Mountain trail

Timber Rattlesnakes are common in this area of the trail.  Signage is posted to remind hikers to be on the lookout and to keep pets on a leash and under close supervision.

Once you reach the top, the spur trail to the right takes you to an overlook with magnificent views of the Catskills where on a clear day, they say you can see up to five (5) states including the Hudson River

The trail to the left takes you to the Fire Tower. 

I went to the left.

For me, it was a welcomed sight!

Fire Tower top of Overlook Mountain Woodstock NY
Overlook Mountain Fire Tower Photo by L. Andrews

Overlook Mountain Fire Tower

Fire Towers were originally built for observers to scan the mountains for forest fires. 

At one time, there were more than 100 Fire Towers throughout New York State.

The Overlook Mountain Fire Tower reaches 60 ft in height.

Overlook Mountain Fire Tower Catskills NY

Views from the Fire Tower include the Hudson Valley, Ashokan Reservoir, and Devils Path.

The tower officially closed in 1988.  It was restored and reopened in June 1999.

Ashokan Reservoir from top of Overlook Mountain Fire Tower
Ashokan Reservoir from top of Overlook Mountain Photo by L. Andrews

Catskills Five Fire Tower Challenge

If you love hiking the Catskills, you may want to take the Catskills Five Fire Tower Challenge!

The Catskill Center through The Fire Tower Project and the DEC manage the six fire towers in Catskill Park (one fire tower is located at the Catskill Center) and opens them each season for the public to enjoy.

The five remaining towers located on mountain summits make up what they call the Five Fire Tower Challenge:

Overlook Mountain – Woodstock NY, Elev. 3,140 ft

Hunter Mountain – Hunter, Elevation 4,040 ft

Mount Tremper – Shandaken, Elevation 2,740 ft

Balsam Lake Mtn. – Hardenburgh, Elev. 3,723 ft

Red Hill – Denning, Elevation 2,990 ft

For completing all five fire tower hikes, you can claim your patch which says you completed the Five Fire Tower Challenge!

If you want to learn more about the Fire Towers in New York state, you will enjoy this book which talks about Fire Towers in the Catskills and the Adirondack Mountains.

I also recommend using the AllTrails app on your phone.

I find it very useful when we are traveling to check out hikes in the area, what the trail is rated, and how to get to the trailhead.

Best Catskill Hikes

Viewing Area At Top Of Overlook Mountain NY
Viewing area at top of Overlook Mountain Trail

Hiking to the top of Overlook Mountain may not be much of a challenge for some hikers.

But for this novice hiker, reaching the Overlook Mountain House, and then finally reaching one of five remaining Fire Towers in the Catskills, was well worth the challenge.

The views from the top of Overlook Mountain Trail are breathtaking and will make you just want to sit there in awe of its beauty.

There are so many Fun Things to See and Do in the Catskills that I hope you add it to your Bucket List of Places To Visit!

If you are planning a trip to the Catskill area, here are more ideas for your trip!

*Best Hikes In The Catskills For Beginners

*Easy Hiking Trail To Kaaterskill Falls – Catskill Mountains

* RV Camping at Nickerson Park Campground

* How To Plan An Awesome Trip To Howe Caverns

*Beautiful Views Of The Ashokan Reservoir Trail – Catskills, NY

hiking overlook mountain fire tower
hiking overlook mountain trail woodstock ny

Pin This For Later!

You may also like

Leave a Reply

Your email address will not be published. Required fields are marked *