Hike Overlook Mountain in Woodstock, NY; Views, Tower, Ruins!

Come on an amazing journey, a hike leading you to the ruins of an abandoned hotel, a tower with 360-degree views, AND multiple lookouts! Let’s hike Overlook Mountain in New York. 😍

If you’re looking for a scenic hike in the Catskills that’s not too difficult with views, a fire tower, AND a super cool abandoned hotel, then look no further than Overlook Mountain in Woodstock, NY.

This post tells you everything you need to know (including a ‘secret’ not to miss view spot!) about hiking Overlook Mountain. (And scroll to the bottom to see the best bakery & spot to get lunch after!🥐☕️)

I had this hike saved on AllTrails for years. Living next door in Connecticut, we drive to the Catskills often when we want a hike with big mountain views. This is now a hike I will return to because I’d love to see it in summer and fall!

The hike up Overlook Mountain is a 5-mile round trip that will take a few hours depending on your speed. The trail starts on Meads Mountain Road and leads you to the ruins of the Overlook Mountain House and a fire tower with stunning views of the Hudson Valley.

With the abandoned Overlook Mountain hotel and the tower views, this hike is the perfect blend of interesting history and amazing mountain views.

🌟It’s a ton of reward for a hike that’s not technically difficult!🌟

Walking up a wide path that used to be an access road for the hotel, the hike to Overlook Mountain is similar to walking on an incline for 2.5 miles.

You’ll love that aside from being a great workout that will get your heart pumping, there is nothing tricky about this hike, making it dog and kid-friendly. I’m sure this is part of what makes it such a popular hike here in the Catskills (get there early!).

Let’s get into all the details and need-to-know info for hiking up Overlook Mountain!

🥾Overlook Mountain Hiking Guide ⛰️

Trail Overview

The adventure begins on Meads Mountain Road in Woodstock, where the Overlook Mountain trailhead is conveniently located. There is a parking lot that fits at least 10-15 cars.

(Note: You don’t have to worry too much about maps and blazes to follow for this hike – you pick up the wide path by the trailhead sign and stay on it the whole time! There is limited cell service here, so if you’d like to keep track of the hike, be sure to download the trail on AllTrails.) 🗺️

You’ll warm up quickly as the almost 1,400 feet of elevation begins as soon as the trail starts!

After about 2 miles of walking on an incline, you’ll reach the Overlook Mountain House – or what’s left of it! It’s a haunting yet fascinating landmark that whispers tales of a bygone era. 👀

It’s hard to imagine that it once housed 300 hotel guests, wow! 🏰 (We go over more history further in the post)

After you check out the Mountain House ruins, you’ll continue on the path beyond the Mountain House (walk past the gate) which will lead you to the tower.

The tower is just a third of a mile beyond the Overlook Mountain House.

At the summit, you’ll be greeted by the Overlook Mountain Fire Tower AND a “secret” view.

To see the secret view take a right on a trail just before the tower – there will be a sign to the right on a tree 🌳 (if you look carefully) that says ‘view’!

After seeing this side view, head to the fire tower where you can climb the secure steel steps for an elevated perspective, offering breathtaking views of the Catskill mountains.

When finished, return the way you came and head back down to the car!

📝 Overlook Trail Details ✅

💚 🔗 ALLTRAILS LINK 🔗

🥾 MILES: 4.6 miles

📈 ELEVATION GAIN: 1,397 ft

💪🏼 LEVEL: Moderate

🚗 PARKING: Click here to navigate to 42.0711, -74.1227

There is a parking lot with around 15 spaces at the top of Meads Mountain Road.

TERRAIN: wide gravel path most of the way up

🐶 DOG-FRIENDLY: Yes.

Given the wide non-technical path, dogs have no tricky spots or scrambles!

KID-FRIENDLY: Yes.

Given the wide non-technical path, there are no tricky spots or scrambles that would be difficult for children.

PEACE AND QUIET 🤫☮️: Depends what time you get here!

We hiked early in the morning on a winter Saturday and were the first ones in the parking lot. We were the only ones up there for a while, but on the way down (around 11am), we encountered several groups of people making their way up.

Given its accessibility, it’s a popular trail so if you want more freedom to explore without many people around I suggest you get there as early as you can!

Overlook Mountain House History 🏰

The Overlook Mountain House, once a grand hotel, is a significant historical highlight of the hike. Initially constructed in the early 1800s, the first lodge was built in 1833 but closed due to low visitor numbers. The allure of the Hudson River Valley drew wealthy travelers, prompting Lewis Wagonen to build a 300-room hotel in 1871. Unfortunately, it suffered from poor business and burned down in 1875.

Determined to revive the site, developers constructed the Overlook Hotel with concrete in the 1920s, aiming to improve fire safety. Despite these efforts, the hotel struggled financially and was eventually sold to New York State in 1940, marking the end of its operation. Today, the hotel ruins stand as a testament to the mountain’s rich history, adding depth and context to your hiking experience.

Wandering around the stone walls and staircases leading to nowhere it’s hard not to let your imagination run free with all this place used to be!

Overlook Mountain Fire Tower 🗼

At the summit, the Overlook Mountain Fire Tower stands tall, inviting you to climb up for an even more breathtaking view.

From its top, you can gaze out over the vast Hudson Valley, appreciating the panoramic vistas that stretch as far as the eye can see.

Before you reach the tower check out the views from the cliff overlook which will be on a “secret” trail heading into the woods on the right before you get to the tower. This eastern-facing cliff would be amazing for sunrise!

And the 360-degree tower views make it an excellent choice for catching the sunrise or sunset. 🌅

Directions & Parking 🚙

From I-87 Exit 19, take Route 28 west and then turn onto Route 375. Alternatively, I-87 Exit 20 provides access via Route 212. Both routes lead you to the trailhead located about 2 miles along Meads Mountain Road.

The parking lot for the trailhead is positioned on the right side of Meads Mountain Road as you travel up. As noted earlier, parking fills up quickly, especially on summer weekends, so arrive early or visit during off-peak hours to secure a spot!

What to do after your hike ☕️ 🥐

At the base of Overlook Mountain you’ll find yourself in the heart of Woodstock, NY – a super charming town with so much to see!

From local shops to numerous cafes and restaurants to art galleries and parks, you spend the whole day exploring and enjoying Woodstock.

After our hike we were naturally starving 😉 so we stopped at Overlook Bakery 🥐 for a couple of sweet treats.

While there we asked the girls behind the counter where we could find the best lunch and without hesitation they said sandwiches at Woodstock Meats. 😍🥪

Leave time before or after your hike to explore and eat in the town of Woodstock. You won’t be disappointed! 🙂 

Summary

In summary, hiking Overlook Mountain in Woodstock, NY, is an adventure filled with stunning views, historical sites, and diverse wildlife. Each season offers a unique experience, and with proper preparation, you can enjoy a safe and rewarding hike. The fire tower and cliff overlooks provide breathtaking vistas, while the ruins of the old hotel add a historical dimension to your journey.

So, gather your gear, follow the directions here, and set out on an unforgettable adventure. Whether you’re seeking solitude in winter or vibrant nature in summer, Overlook Mountain has something for everyone.

Happy hiking! 🩷🩷

Frequently Asked Questions

Can you climb the Overlook Mountain Fire Tower?

Yes, even in the winter, we were able to climb several flights up the Overlook Mountain Fire Tower, it offers breathtaking 360-degree views of the Catskills. Enjoy stunning views of the Catskill mountains all around you.

Where is the plane crash on Overlook Mountain?

You’ll find the plane crash ruins on Overlook Mountain just south of Kaaterskill’s summit along the trail to Hurricane Ledge. It’s definitely worth a visit!

What is the history of Overlook Mountain?

Overlook Mountain’s history is rich, starting with the first Overlook Mountain House built in 1871, which burned down and was rebuilt in 1878. Additionally, in 1902, the southern slopes hosted the Byrdcliffe Colony, known for its arts-focused utopian community.

How long does it take to hike Overlook Mountain Woodstock?

It usually takes about 2 hours and 47 minutes to hike Overlook Mountain, which is a 4.6-mile trail near Woodstock. So, if you’re planning a trip, just set aside around 3 hours for the hike!

How long is the hike to Overlook Mountain?

The hike to Overlook Mountain is about 5 miles round trip and typically takes around 3 hours to complete. Happy hiking!