Overlook Mountain Hike - Ruins, Fire Tower, and a View - Catskills, NY

By the beginning of the summer of 2018, I had finished my New England High Peaks and I vowed to venture out of the six states we refer to as New England.  Until this summer, I paid little attention to the Empire State outside of trips to New York City, days spent watching the horses race at the Belmont, or to spend some time at the beach in the Hamptons.  When July rolled around, I wanted to spend some time in the woods of New York - I wanted to soak in the streams, float in the lakes, hike wooded trails, and drive through those quiet back roads.  Dreamy, right?

 It all started with the Adirondacks as I convinced my parents that this part of New York was worth four days during fourth of July.  They enjoy anywhere with a 50 amp service for their RV, so off to Ausable Chasm in New York we went.  We spent the holiday hiking, eating, camping, rafting, biking, drinking, and swimming through northern New York.  After this trip outside the city and Long Island limits, I was hooked. 
Gimme all those mountain views and lazy streams.

After four days in ADK, I wanted to see more of New York and I set my sights on a weekend in the Catskills. Why the Catskills?  Great hiking, scenic towns, and let me be honest, a closer drive than the Adirondacks (4+ hours each way to where we camped is fine for a long weekend, tough for a day or two).  My original plan was to spend the entire weekend in the Catskills, hiking Kaaterskill falls and exploring some of these quaint little towns and breweries.  Instead, I turned my weekend trip to the Catskills into a day trip, and convinced a man and his dog that five hours of driving was totally worth it for a five-mile hike.  Side note:  they weren't hard to convince.  

This road trip also involved a stop in idyllic Salisbury, Connecticut for coffees and chocolate croissants at charming Sweet Wiliams Bakery (also mentioned in my Bear Mountain post- it's that good)

This trip, like the Adirondacks, confirmed that New York is a beautiful state I need to spend more time in.  Saturday in the Catskills was the perfect reminder that with the right company the drive can be the best adventure, that your road sodas should be less than 9%, and dogs make every hike (and brewery trip) so much better.  

Overlook at Overlook Mountain

A good workout with some decent elevation (constant incline up an old gravel road).  Overall, a nice hike with rewarding views at an easy distance.  This dog and kid friendly trail has three highlights:  the old hotel ruins, the overlook, and the 360-degree view from the fire tower.  The hotel is a great spot to stop and take a few photos and walk around the old and impressive ruins (read about its history first).  The overlook was small and crowded but provided a great view of the Hudson River and the valley below (although a bit hazy the day we hiked it).  The fire tower offered a great 360 view (with an awesome map inside the tower) of the Catskills below.  It was a less than exciting trail but with cool history and great views.  The surrounding towns have some great areas to explore.  We sort of forgot to check out Woodstock and Saugerties and instead, spent the afternoon sipping local beer while our dogs snoozed and knocked down a few kids (don't worry, they got right back up).  

Overlook Mountain House Ruins 

Rob and Rogi at the overlook - because Olive wouldn't pose with me 

Trailhead: Overlook Mountain TH, 335 Meads Mountain Road - Woodstock, NY

Trail:  The trail itself isn't very exciting, as it follows an old gravel road up to the hotel.  It is a popular trail so not the best hike if you want solitude. At around mile 2 past the hotel, the trail splits, left to Echo Lake or straight/right to the overlook. At about 2.3 miles, you will pass an old ranger station right by the overlook - the trail is easy to follow.  

Distance: 4.8 miles RT (out and back hike) 

Elevation Gained: 1,394 feet

Summit Elevation:  3,140 feet

View: From the fire tower, you have awesome views of the Hudson River, Ashokan Reservoir, Westkill Mountains, Indian Head Mountain Range, and Overlook Mountain.

Dogs: Yes, on-leash

Kids: Yes 

Parking:  Parking can be tough as this is a popular trail and the lot fills up fast.  The main parking area at the trailhead (about 30 cars) is across from the Buddhist temple.  We were lucky and caught someone leaving as we pulled in.  The lot at the trailhead is small but, a new trailhead on Macdaniel Road, about half a mile from the Overlook Mountain Trailhead, provides additional parking.  A new trail that’s about seven-tenths of a mile long connects the two trailheads.

Skill Level:  Easy to Moderate (incline and distance)

Red Tape:  Some of the trail traverses through timber rattlesnake territory (by the hotel ruins).  Be aware, keep an eye on kids and dogs and stay away from the rocky areas by the ruins. 

Mountain House Ruins

Overlook Mountain House

The ruins towards the end of the hike are actually the remnants of the third building erected at this site.  The first building here was a small lodge built in 1833.   The lodge closed after a few years and a new developer rebuilt and reopened the hotel in 1871 with some serious upgrades as a 300-room hotel.  However, the business was slow and unfortunately, the hotel burned down in 1875.  In 1892, Otis Elevator Company built a cog railroad from the valley floor to the mountain top to make the journey easier and quicker.   However, when Henry Ford created the automobile, the need for the cog train was no more and the train and tracks were sold for scrap in 1918.

After the second fire, the hotel was rebuilt by two brothers in 1878 and sold to a hotelier in 1917 (this time with concrete).  Sadly, the Overlook burned down again in 1921 before it was even finished.  The ruins along this hike is all that remains of this once famous hotel.  Many historic resorts that called the Catskills home were destroyed after they closed.  However, this mountain house, framed with concrete, still stands today.  The ruins nestled in the mountains are an eerily beautiful example of nature taking her territory back and the old hotel makes for a great lunch spot on your way back down the mountain.  More photos of the original mountain house. 

Fun fact:  Three American presidents visited the hotel (Grant, Arthur, and T Roosevelt)

Fire Tower at Overlook Mountain

Sign Marking the Fire Tower as a National Historic Lookout

View from the Fire Tower 

My favorite way to end a great hike is at the local brewery- preferably with a flight of cold local beer I have never tried before.  Before we left for the Catskills, I did some research on dog-friendly breweries and had a list ready for the car (welcome to travels with Katie!).  Both breweries I decided on were dog-friendly (even inside!) and were the perfect way to chat about everything and nothing while the pups napped and the humans drank.  We started at Keegan Ales in Kingston and enjoyed a flight and a few pints.  Nothing hit us as being amazing, but we enjoyed the variety of decent beer and the atmosphere of the brewery.  

Two tired hound dogs after a hike

First brewery stop - Keegan Ales 

Flight at Keegan Ales 

Our next stop was at Hudson Ale Works in Highland, New York.  I loved the fun and quirky beers ranging from a coconut porter to a green tea ale (which we jokingly called weed beer for the first half of the tasting).  You can tell I was having too much fun (read drunk) by the lack of photos and specific remarks on the beer (sorry, mom).  Again, they were dog-friendly (inside and out) and we spent an awesome hour or so, sipping beer on the comfy lounge furniture on the patio.  

Great company, an awesome hike, and a few brewery stops along the way.  

This day in the Catskills, oh it was a good one.