Day Hike in the Catskills: Overlook Mountain Trail

If you’re looking for a great day hike in the Catskills, the Overlook Mountain Trail provides a fulfilling mix of exercise, views, attractions, and proximity to good food and drink. In all fairness, that describes a lot of trails in the Catskills, which is why we enjoy heading up there for day hikes. Especially since there is nothing remotely comparable in our home state of New Jersey. 

Quick Synopsis: 

This hike offers a steady incline that is steeper toward the beginning before calming a bit near the top. Because the trail is an old road it is wide and it’s easy to distance from others or pass/be passed. We are just two people but the wide dimension makes it great for families or bigger groups.

We also saw lots of people with their dogs who seemed to manage well. Microspikes in the winter will make it a lot easier than just hiking shoes or sneakers. The three main attractions (hotel ruins, fire tower, and cliff views) did not disappoint and proved to be a unique experience. 

In the summertime you have to watch out for Timber Rattlesnakes, which can be found anywhere from the parking lot to the peak. This should go without saying, but touching the rattlesnakes is bad. Strongly do not recommend.

The narrative below is a detailed discussion of our itinerary and experience of the day, but if you want the basic facts of the hike you can jump to Outlook Mountain Trail Hike Details.

Itinerary and Experience:

The month of January this year was cold and snowy. So when we had a warm(ish) sunny day on our weather report, we decided to take advantage and head to the Catskills for a day hike on one of the many snow-covered trails. We took the 2.5 hour drive from our beach-living New Jersey apartment up the winding roads (aka the Garden State Parkway) to New York’s lush and beautiful Catskill mountain region to the Overlook Mountain just outside of Woodstock. 

We chose the Overlook Mountain Spur Trail because of the distance and length of time it was estimated to climb there and back. Our full day was a little less than 12 hours, which included 2.5 hours there, about 3 hours on the trail, 45 minutes to the brewery, 2 hours at the brewery, and 3 hours back home.

We fed Snoop and were on the road by 7:15 a.m. with coffee. Lots of coffee. But not too much because then we’d have to pee while hiking. It’s always a careful dance. 

We made it to the parking lot at the Overlook Mountain Spur trailhead on Meads Mountain Road a little before 9:45 am with several parking spaces still available (not always the case). We stepped out of the car and almost fell flat on our ass as the ground was a sheet of ice. Thank goodness for microspikes and hiking poles.

Up We Go

We began upwards, passing a group who were deciding whether or not to head on without microspikes. We were almost the only people on the trail up, going back and forth with a woman and her dog who did not seem bothered at all by the hill and ice. The trail is wide and open, following what used to be a road up the mountain. The incline is continuous and relentless, hardly leveling out at all. Lots of breaks were needed.

In the winter when there are no leaves on the trees you can see out to the other various mountains and peaks. The sparse foliage makes for great views on the way up. Also something to look at while trying to catch your breath and stabilize yourself so you don’t roll down the hill. Although if we had a sled I definitely would have done that coming down. Packable sled, anyone?

Hotel Ruins

While relentless, it did not take too long to get to a reward. After about an hour, we looked up and saw the ruins of an old hotel appear before us. Not quite at the peak, this feature made this hike unique – while the official park website directs people to stay out of the ruins, the structure is open air, allowing us to walk about the skeleton of the building. (Although as a disclaimer, we advise you to listen to all official notifications and directions regarding safety!) It’s not often you stumble upon ruins in a forest, especially ones as big as these, and we spent quite a bit of time walking around them. We also love history so this was right up our alley. 

The trees are growing up and through the open windows and the floors are long gone. The remains of a fireplace and a stairway to nowhere give hints of what once was. You definitely need to watch your step as it would be easy to fall down into the lower levels on the right hand side. We spent a lot of time wandering through the hotel, only to walk out the back and find another building: the shell of a lodge that had begun construction but was never finished. 

History of the Overlook Mountain Hotel

As we’ve noted before, we love history, so we are always curious to research and learn the story of a place. But if you’re here for the hike, click here to bypass this section!

The ruins are of the old Overlook Mountain Hotel. The crumbling structure in front of us was the third iteration of an ill-fated luxury resort. It first opened in 1871 and was developed by Lewis B Van Wagonen during the peak of vacation activity in the Catskills for New York’s wealthy socialites. The 1800s was a time of growth in the Catskill region as writers, poets, and artistic folks alike descended on the wilderness. 

Given the growing popularity of the mountains, many luxury hotels were built during the 19th century, trying to entice people from the city to come spend money in these little mountain towns. 

The 300-room Overlook Mountain hotel played host to President Ulysses S. Grant in 1873, but success was short lived as the hotel burned to the ground on April Fool’s Day in 1875 (as the story goes, no one believes it was on fire because it was April Fool’s Day – oops).

The owner sold and two brothers tried again in 1878. With the improvements of train technologies and rail lines now coming up into the mountains, the hotel was easier to access and enjoyed more success for the next several decades before – you guessed it – burning down a second time in 1923. This time the new owner, having learned from history, worked to rebuild with a stronger material – reinforced concrete. Construction began in the late 1920s but financial troubles and the proprietor’s death led to an abandonment of the project by 1939. The land was ultimately sold to New York State in 1940, and the trail opened in the 1970s for the public.

Another two fires in 1941 and 1970 left the Overlook Mountain Hotel without interior walls, a roof, or windows, but it is one of the only remnants of the Catskills heyday as many of the other hotels of similar vintage were demolished. 

The date 1928 (year construction began) is carved into the lintel above what would have been the main entrance.

Back to Some Hiking

After taking a significant amount of photos and roaming in and out of the crumbling structures, we continued up along the trail. The break to explore the ruins gave my legs some much needed downtime. The remaining 15 minutes to the peak felt easy. 

There is a trail junction just past the ruins at mile post 1.99. If you veer left you will head toward Echo Lake, another 2.25 miles out. We did not do this extended hike but have heard Echo Lake is beautiful if you have the time.
Bearing left will also lead you to Codfish Point, before bringing you back down to Platte Cove and the trailhead there. The Platte Cove trail offers additional trail junctions toward the Devil’s Path as well. 

For this day trip we stayed right, continuing to follow the former road upwards to the fire tower and cliff views.

Fire Tower

The fire tower was constructed in 1950 (this probably would have been helpful to have during the many previous fires) and seemed to all of a sudden appear out of nowhere to the left of us. The tower sits at 60 feet tall on top of an elevation of 3,150 feet above sea level. The newspaper article published the week before the tower opened claimed that from the top of the tower, one can see 200 miles in any direction on a clear day. 

I don’t know if we were seeing 200 miles but it was an absolutely breathtaking 360 degree view, although the wind could have taken us down in a second if we weren’t paying attention.

We ate some lunch at the picnic table at the base of the tower (pb&j sandwiches!) and gave ourselves another little rest. There is a small ranger station near the tower that apparently has a museum associated with it, but it was closed when we were there.

Following to the right of the ranger station the trail leads on.

Overlook Mountain Cliffs

This short walk brings you to the Overlook Mountain cliffs, which also offers a stunning view of the surrounding area. It’s a peaceful place to sit for a while, eat a snack, and just take it all in (although definitely be careful as this is a fairly sharp dropoff). People have carved their names into the rocks here, some going back to the early 1900s. 

After enjoying the view and a rest, we began the trek back down the mountain. The microspikes and hiking poles made this a much easier way down than it would have been without the equipment.

The trail was also getting a lot busier – on the way up we saw a couple people coming down and ran into a few at the fire tower but we mostly had the place to ourselves. Now, it was a constant flow of people. We saw the same group who had been deciding whether to move on without microspikes. The entire group had microspikes so clearly a decision was made to go purchase some new gear. 

When we got back down to the parking lot it was equally packed. Cars were lined up down the road. The early morning travel (and it wasn’t even that early compared to some) was well worth it to avoid the crowds.

Food Time!

Hiking takes a lot out of you, and we always enjoy ending a day hike with good food and drink at a local establishment. There are a lot of great places to stop in the Catskills. Today, we headed over to West Kill Brewing in West Kill, NY (aptly named).

This brewery is located on a historic dairy farm and is home to a fabulously beautiful brewery cat named Teddy.

The temperature was dropping now that the sun was going behind some clouds. We also weren’t hiking up a vertical mountain road, so we grabbed a seat inside by the fire. A food truck parked outside provided us with some much needed sustenance. John went for a  vegetarian chili and I couldn’t pass up the pulled pork sandwich.

I am not a big beer drinker. No matter how hard I try to pretend I am, I cannot hop on board with hoppy beers. (See what I did there). West Kill has a great assortment of non-hoppy options, including a mulled wine, served warm. My perfect companion to John’s hoppy beer paradise. Alongside one of the best pulled pork sandwiches I’ve ever had, it was a great way to end the day. 

Sum Up

For a 3-hour hike with stunning views and unique attractions, you really get a big bang for your buck. Checking the conditions ahead of time is key in the winter. We would have been miserable without the microspikes and the hiking poles were really helpful. John found a Facebook Group called Catskills Trail Conditions that was helpful. Also, the AllTrails website provides good details and advice. 

I love a place with an interesting history and the Overlook Mountain Hotel ruins did not disappoint. While it is steep the whole way, the hike is not too long. The three main attractions at the top are worth the effort.

Outlook Mountain Trail Hike Details

Trail Length:	4.6 miles round trip
Hours to Complete:	3 ish – depending on how much time you linger at the attractions
Elevation Gain:	1,397 feet
Difficulty:	Moderate (on a scale of Easy to “did McKinley die” we rank this one a “needed breaks but made it without incident” level of difficulty)
Hours Opened:	Open Year-round
Best Time of Day to Go:	First thing in the morning to avoid crowds
Location:	Woodstock, NY
Trailhead:	Overlook Spur Trail from Meads Mountain Road – 353 Meads Mountain Rd, Woodstock, NY 12498
Route:	Out and back; however, can continue on for longer hike
Dogs Permitted?	Yes
Unique Attractions:	Hotel Ruins, Fire Tower, Cliff Views
Activities:	Hiking, Biking, Snowshoeing, Downhill Skiing
Camping Permitted?	Primitive camping allowed – campsites must be at least 150 feet away from nearest road, trail, body of water. More than 3 nights or groups of 10 or more will require a permit
Recommended Gear:	If you go in the winter, check conditions ahead of time. Microspikes and poles were key for our February hike. Did not need snowshoes this time but it’s a possibility
Things to watch out for:	Rattlesnakes – seriously 🐍😳