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How To Do New York’s Overlook Mountain Hike For Amazing Catskills Views

By Adrien Behn. This post on hiking Overlook Mountain contains affiliate links to trusted partners!

Looking to do the Overlook Mountain hike in the Catskills Region of New York?

Then you’re in the right place!

The Catskills is known for its refreshing bucolic atmosphere, tiny artist towns, and inspiring strolls through the woods.

Wandering through the Catskills has been a source of inspiration for painters, writers, and photographers alike for centuries. Historically, this region has been a notorious space for artist retreats and an escape from city life. 

The old mountains here are iconic to southern New York and the Hudson Valley, with the Catskills Region featuring 5,892 square miles of protected forest showcasing more than 30 peaks that stretch over 3,500 feet high, making it heaven-on-earth for hikers.

Pro tip:

To really feel like you’ve stepped out of a Thomas Cole painting, gaze out toward the Catskill Escarpment range, which forms a stunning silhouette of glaciated mountains begining on the western edge of the Hudson River.

In terms of location, you can find the rolling hills and towering mountains of the Catskills about 100 miles from New York City and 40 miles from Albany in the famous town of Woodstock, which sits at the base of Overlook Mountain and is the perfect location to get outside for the weekend.  

Something else neat:

The Catskills are filled with strange secrets. From the legend of Rip Van Winkle to the remains of a plane crash near the Kaaterskill High Peak Trail, treks in the Catskills offer a myriad of surprises.

Overlook Mountain delivers on the unusual easter eggs left for hikers to explore outside of bird watching.

Ready to lace up your boots and hit the trail? Read on to learn more about hiking Overlook Mountain!

Pro tip: Before going hiking, make sure to download the AllTrails app to have trail guides, maps, photos, and reviews right at your fingertips. You can also sign up for a free trial of AllTrails+ to download offline maps, get alerts for wrong turns, find trails by distance from you, and more!

What Type Of Hiker Are You? [Free Quiz]

But first, before we dive into our Overlook Mountain Catskills guide, I want to share a free personality quiz I think you’ll love.

It’s called “What type of hiker are you?” and it will help you discover your hiking personality. Bonus: Your results also share trail suggestions based on your quiz responses!

On that note, let’s dive into how to enjoy one of the best hikes in the world!

Overlook Mountain Hike Quick Facts

Below, I’ll be sharing my riveting hike of Overlook Mountain — one of the best hikes in Upstate New York and a must-mention in any Catskills travel guide.

But, first, here are some quick facts about the hike so you don’t go wandering off into the forest aimlessly and get picked up by the fairy people. Hey, there is some weird stuff in the woods when you go off the trail:

Price: Free

Trail Difficulty: Moderate 

Trail Length: 4.6 miles round-trip 2.3 miles one-way

Trailhead: Take the Overlook Spur Trail from Meads Mountain Road. The official address of the hike is 353 Meads Mountain Rd, Woodstock, NY 12498.

Overlook Mountain Trail Highlights:

  • Exploring the beauty of the Overlook Mountain Wild Forest
  • Seeing the historic Overlook Mountain House ruins
  • A stunning valley and mountain view at the end of the Overlook Mountain trail
  • An even higher view from the top of the Overlook Mountain Fire Tower

Getting To Overlook Mountain From NYC: By car, Overlook Mountain is a two-hour drive from New York City on I-87 N highway. If you don’t have a car, you can take the Metro-North up to the Poughkeepsie train station and take the Z-WBZ Regular 2020 bus to Woodstock. Or you can start warming up now and walk for 36 hours. Whatever is most convenient for you. 

When To Hike Overlook Mountain: The trail is open year-round. Anytime from April-November will give you amazing views of wild flowers and/or foliage. That being said, you can absolutely snowshoe this trail in winter, as you’ll see from some of the photos below. It’s honestly one of the most fun things to do in the Catskills in winter.

Extending Your Hike: A popular addition to this hike is to continue on to Echo Lake (part of the Indian Head Wilderness), which would bring this trek to about 8.5 miles round-trip.

Camping: While there are no designated campsites in the Overlook Mountain Wild Forest, primitive camping is allowed. Many people enjoy camping near Echo Lake.

Woodstock Location + Overlook Mountain Trail Map

Woodstock is located in the Catskills Region of New York State. More specifically, it resides within the northern part of Ulster County near other great destinations like Kingston, Mount Tremper, and Phoenicia. These all make for great solo, family, group, and even romantic getaways in Upstate New York.

You’ll also be near epic hiking trails like Slide Mountain, Giant Ledge hike, and, of course, Overlook Mountain.

Click here for an interactive Overlook Mountain trail map.

Overlook Mountain trail map

Overlook Mountain Hike: What To Expect

Now that the logistics are out of the way, let’s dive into what you can expect when hiking Overlooking Mountain.

I grew up in the Hudson Valley but somehow never managed to explore the iconic hikes of the Catskills until I left.

Last spring, when the pandemic hit my adopted home of Brooklyn, my partner and I impulsively decided to quarantine on a sheep farm right outside of the Catskills. What was planned to be a two-week stay morphed into six months.

As the world began to warm with lockdowns still enforced, we needed a way to get out of our tiny cabin without breathing on anyone else.

And so, on a rainy April day, we decided to drive south for an hour to Woodstock and hike the 4.5-mile out and back trek of Overlook Mountain. 

Seeing sheep in Woodstock being hiking Overlook Mountain
Idyllic scenery in the Catskills, New York. Photo via Adrien Behn.

Once we got into Woodstock, we drove up the serpentine Meads Mountain road, which was dripping with spring. Dogwoods, magnolias, and crab apples were in full bloom. Heavy white and pink blossoms draped over branches like doilies.

After driving at an incline for 10 minutes, we were welcomed by the trailhead — and a Buddha statue.

Next to the parking lot and near the Overlook Mountain trailhead is Karma Triyana Dharmachakra, a Tibetan Buddhist monastery right in Woodstock.

The outside space was lined with multicolor Tibetan prayer flags, matching the wildflowers that were starting to wake up after a long winter slumber. For a moment, you couldn’t convince me we weren’t in Tibet as a cold spring wind wrapped around us. We bowed in respect and hit the trail. 

On Meads Mountain Road, we followed the red marked Overlook Spur Trail path towards the Overlook Mountain Fire Tower, our goal destination.

Fortunately, due to the weather, there were hardly any cars in the parking lot; however, know that when it’s nice out it does fill up quickly, and if you park outside of the lot you can get a ticket. You have been warned. 

Mossy landscapes during the Overlook Mountain hike
A moss patch or a gnome grove? Photo via Adrien Behn.

The path up to the top is a long and wide gravel road — not the pastoral skipping through the woods most would expect. That is the thing with the Overlook Mountain trail; you’re really working for the reward at the top.

I swatted a mighty mosquito on my partner’s neck. They were out early this year and thirsty. We trudged along the inclining road and saw power lines criss-crossed over red maple and balsam fir trees.

The path is just straight up, no switchbacks or tight curves. Again, you’ll want to keep your eyes on the prize — as in, the view at the top!

Note that if you’re bringing your pup dogs do have to be kept on a leash — though that didn’t stop one guy and his black lab from jumping in a small pool close to the entrance. If you do decide to step off the path for a moment, you will find that fairytale land of mossy boulders and miniature ponds. 

Overlook Mountain Hike scenery
Overlook Mountain Hike scenery. Photo via Adrien Behn.

Overlook Mountain House Ruins

We continued walking uphill and inhaling the air misted with fresh rain, and after about 1.7 miles we came to the remains of the Overlook Mountain House Hotel.

The property was built in the 1800s when numerous resorts and luxury hotels were constructed to capitalize on wealthy New Yorkers traveling north for respite and relaxation. Hey, not much has changed.

But the Overlook Mountain Hotel never had a chance. Although the views are jaw-dropping, getting there was a struggle for people due to its remote uphill location.

After 100 years, two fires, slow business, and one last haphazard reconstruction, the hotel was sold to New York State.

Overlook Mountain House Hotel ruins
Overlook Mountain House Hotel ruins. Photo via Glarkin53/Wikimedia Commons.

The irony is with so many visitors hiking the trail, the dilapidated Overlook Mountain House Hotel gets more action now than it did when it was operating.

It is also one of the only remaining sites featuring architecture from that time since so many of the other luxury resorts were torn down and sold for scrap.

Today, hikers can take a breath before the last push to the top of the mountain and wander around the crumbling rooms. It’s some fine derelict scenery.

Stunning Overlook Mountain Views

Although the path isn’t mesmerizing and is an uphill challenge, when we reached the top we realized the work was worth it.

The view — which you’ll take in from a rock ledge accessed via a narrow trail behind an information cabin — is absolutely stunning, extending out over the Catskill Region toward the Ashokan Reservoir.

You can see stretches of the Hudson Valley and the Hudson River itself flowing down from the Adirondacks and making its way to the Upper New York Bay.

Actually, on a clear day you can see up to five different states from here!

Views From The Overlook Mountain Fire Tower

If you want an even higher view, muster whatever energy you have left and head to the top of the Overlook Mountain Fire Tower, one of the few public fire towers in the Catskill Forest Preserve.

The 60-foot climb is nothing compared to what you’ll already have done and the views open up with an expansive vista of the Hudson River Valley.

From 3,140 feet, you can see miles of red oaks and conifers, sweeping views over the the Hudson River Valley, the Ashokan Reservoir, the challenging Devil’s Path hking trail, and the Berkshires in Massachusetts.

Honestly, even the Hudson River looks swimmable at this distance — though I don’t advise jumping in to cool down!

Overlook Mountain Fire Tower
Overlook Mountain Fire Tower. Photo via Niranjan Arminius/Wikimedia Commons.
View from the Overlook Mountain Fire Towe
View from the Overlook Mountain Fire Tower. Photo via Mister.ev/Wikimedia Commons.
Overlook Mountain hike view in winter, Woodstock, New York
A view from Overlook Mountain in winter. Photo via Jessie Festa.

For reasons unknown to me, some days the fire tower is locked, so just be aware of this.

If you want to bring snacks and drinks there are a few picnic tables to crack open whatever you schlepped up with you.

Note: While we didn’t see it on our hike, there is apparently an Overlook Mountain plane crash site if you know where to look, at least according to AllTrails.

As we made our way back down, we tried not to let gravity overtake us as we talked about the burgers we were going to devour when we got back into Woodstock.

Overlook Mountain trail moss
So much moss along the Overlook Mountain trail. Photo via Adrien Behn.

Exploring Woodstock, New York

Woodstock has a lively and walkable town center with locally-owned boutiques, co-ops, bookstores, spiritual shops, art galleries, restaurants, bars, and cafes, making it a popular option for those wanting to explore New York State travel.

You will still see the occasional hippy who has seemingly been left behind by his friends 52 years ago, musing the streets and still singing Jimmy Hendricks.

In the town center there are also benches and picnic tables to gather and eat at, which is where we chowed down on tasty burgers from Shindig.

Exploring Woodstock after hiking Overlook Mountain in the Catskills
Wandering the shops of Woodstock, NY. Photo via Jessie Festa.

Honestly, though, this is just one of many great eatery options, a few others of which include:

  • The Mud Club. Part cafe, part cocktail bar, there are loads of indoor and outdoor spaces to enjoy your food and drink. With loads of giant trees, wooden seats, and dangling fairy lights it has a magical feel.
  • Oriole 9. Their delicious breakfast and lunch dishes feature produce from the owner’s garden. Avoiding meat or just want to try something unique? Their Tempeh Reuben is delicious!
  • SILVIA. The menu here features delicious dishes made with local and sustainable ingredients. They’ve also got a creative cocktail menu of drinks like the “Orange Jalapeno Shrub Fizz” made with Denizen Aged Rum, cider vinegar, coriander, and club soda.

After you eat, get an aura reading, peruse psychadelic goods at the head shops, or, if it’s the evening, see a show at the famous Levon Helm Studios, a fun music venue owned by Levon Helm of The Band.

Tips For Hiking Overlook Mountain Woodstock

Here are a few additional tips for hiking the Overlook Mountain trail:

-New York is beautiful and verdant, which also attracts pests of all kinds. Bring bug spray to combat mosquitos and check yourself for ticks after.

-While you’re on the hike, keep an eye out for Timber Rattlesnakes. These reptiles can get up to four feet long and are the most venomous snakes in New York State.

-Bringing a dog? Make sure to keep them on a leash — especially if you want to avoid injury from one of the Overlook Mountain rattlesnakes I just mentioned, which are not uncommon to see.

-Note that while people do often explore the Overlook Mountain Hotel ruins, technically you are not supposed to, according to the Department of Environmental Conservation website.

-Always check the Overlook Mountain Weather Forecast so that you have the appropriate gear.

-As this is a popular trail, it can be a good one for those hiking solo. Check here for important safety tips for hiking alone.

Where To Stay In Woodstock, New York

Click here for a full list of Woodstock NY hotels!

Prefer self-contained stays? 

Click here to check out unique local rentals!

You can also use this map to search for local stays:

Tours In The Catskills

Click here for a full list of Catskills tours & activites!

Renting A Car In The Catskills

The best way to explore all that The Catskills has to offer is by car, as many hotels, trails, and attractions aren’t within walking distance and public transportation isn’t a common way to get around locally.

My recommendation: Use Discover Cars to quickly compare your car rental options.

Their comparison tool does the homework for you, so there’s no need to have up 10+ tabs trying to figure out which company is the most affordable. Actually, you can save up to 70% using their tool!

Other Great New York Hikes:

The Giant Ledge Panther Mountain hike isn’t the only great hiking trail option in New York State. Some others to check out include:

  • Anthony’s Nose Hiking Trail. This moderate hike offers sweeping views of the Hudson Valley and Bear Mountain State Park from the top.
  • Mount Marcy. This challenging hike takes you to the top of the highest peak in New York, Mount Marcy, at 5,344 feet! Warning: You’ll need to essentially climb toward the end, or at least hike vertically, but it’s worth it!
  • Mount van Hoevenberg. This moderate but steep trek ends with panoramic views of the Adirondack High Peaks Region.
  • Bull Hill Full Loop. The views of the NYC skyline from the top are incredible on this hike.
  • Breakneck Ridge. A challenging hike with some vertical climbs that offers amazing views along the way.
  • Bear Mountain State Park. This popular park is full of hiking options as well as areas for fishing, picnicking, and other outdoor activities. One of my top solo hiking tips would be to head here, as you’ll find plenty of safe and populated trails.
  • Slide Mountain Trail. This is a great option if you’re looking for other Catskills hiking trails, as Slide Mountain is the highest peak in the region.
  • Giant Ledge. One of the most scenic hikes in the Catskills, as you take in expansive views from multiple ledges.

New York Travel Insurance

When visiting New York — or anywhere else in the world — make sure to get travel insurance.

One of the best travel medical insurance for travelers is SafetyWing as they’ve got a large network and offer both short-term and long-term coverage — including coverage if you’re traveling for months as well as limited coverage in your home country).

Additionally, SafetyWing is budget-friendly and offers $250,000 worth of coverage with just one low overall deductible of $250.

Click here to price out travel insurance for your trip in just a few clicks.

Have you done the Overlook Mountain hike?

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About Adrien Behn

Adrien Behn is the creator and host of the travel podcast, Strangers Abroad. It is a series of conversations she had with strangers she met while backpacking, where she discusses travel advice, self-growth, and stories from abroad, focusing on the importance of getting out of your comfort zone. She is also a live stage storyteller and can bake a mean pie.

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