Love hiking here! If you're in this part of the Catskills, I highly recommend this trail. It's easily accessible and an easier hike to do. The trail is well-groomed and very walkable. There aren't any scrambles or large boulders, which is good.. The view from the top is pretty epic, and the fire tower which has been closed every time I've hiked the mountain has great views too. I would highly recommend this hike. read more

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This place is absolutely amazing! I've hiked all the Catskills mountains three times over through the years and I had never been to overlook because there was no reason to but I had heard so much about this location I just had to visit and satisfy my curiosity on why this place is so popular. First off the parking lot is medium sized and parking on the road (even off the road) is risky because certain spots you are not allowed to park so arrive early, get a legit parking spot and save yourself the wasted trip or the hassle of returning to your vehicle to a ticket or it completely gone (towed). The hike up and back for Overlook is approximately 5 miles so everyone is spot on mentioning the distance. It's fairly steep all the way up and while you don't have any views on the way up, you do encounter some old ruins which is a neat break along the way. Once you do make it to the top you are met with a small shed that has some very minor historical information inside and on peak weekends you'll find stewards that can assist with information about the area and hiking tips. The fire tower can't be missed to the left after the small shed and the view is to the right of the shed. I have to say, I've been atop many mountains and it's been a long while since I've had my breath taken away but when I saw the view at Overlook it was breath taking. What made the view so beautiful and different than other mountains I've hiked is that the view is expansive with no mountains obstructing so you can see as far as the eyes can see. It's truly a remarkable view being so high up and seeing so far out. This mountain is known for its rattlesnake population. Sadly I never got to see one because I always hike in the early morning hours and they normally come out at around high noon when the sun is the hottest. read more

The hike itself is a slog in both directions -- long stretches of steady slope on gravel. The path's otherwise unadorned; there's little to see for 90% of the journey aside from foliage. But, once you get to the stuff worth seeing, it's soooo worth seeing. I had an inkling of what to expect, having scanned some other reviews and write-ups about this hike, but nothing prepared me for the real deal. Definitely explore the ruins of an abandoned hotel. Don't skip past the easily-missed scenic overlook. We came on a weekday morning and effectively had the vista ledge and fire tower to ourselves. I'd imagine that during the summer and on weekends, this trail can get crowded quickly. Even still, the small parking area right by the trailhead was nearly at capacity when we arrived and when we departed. Perhaps our favorite memorable moment was greeting an elderly fellow on his way down the mountain... only to be lapped by him again going BACK up the mountain not long after. One roundtrip was plenty for me in a day -- this guy must have been part mountain goat; we were in awe of his stamina! read more

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There's no doubt about it- the Catskill region is home to some stunning mountain peaks- and Overlook Mountain is part of it. If you're hanging out in the Woodstock area, you might as well drive further up here to get that 'postcard' feel. This mountain is a popular place and it's for whatever you want it to be: die-hard hikers, quads/leg day or just take in Nature. Either or, whatever brings you to Overlook, make the 2+1/2 mile hike (from starting point) and see the shell of Overlook Mountain House (hotel) from centuries ago. We always use this part as our landmark to catch our breath, sit a bit and really get a glimpse of the hotel that was. But if your legs aren't wobbly enough after that excruciating hike, tackle the challenge (only 1/2 mile more) and head to the summit for that incredible and breathtaking Catskill mountain view. read more

A beautiful place to go hiking, we didn't even go up to the top. We just stayed on the lower trail, but we really liked it. Would love to go back. read more

This hike is BORING. The hike up the mountain is on a gravel road that just stretches on forever until you reach the hotel ruins in the mountain. After that, it's another 0.5 mile to the top. The view from the fire tower is fantastic and makes up for the boring hike. The very top is locked when I went in the morning, but you still get an amazing view. Also make sure to checkout the overlook which is just a few hundred feet from the fire tower. I came here solely for fall colors and it was really worth it. There is limited amounts of parking at the trailhead, which means there are limited number of people who can be at the summit. Makes for a more tranquil experience. Note: I heard there is a $150 fine for parking along the road so be warned. read more

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Its a hard hike up but the best view Ive ever seen. Don't underestimate the hike up and you'll be fine.

One of my favorite trails out of all my hikes! But definitely not for everyone. Went in late July and the weather was perfect, breezy and sunny. Overall the trail is great for any skill/experience level hikers since most of the terrain is a light gravelly incline all the way to the top. No fun scrambles or tricky parts, just brute force your way up and enjoy the various landmarks and views- ruins of a hotel halfway on the trail, wide mountaintop view of various states, 360 view from atop of a fire tower. Parking - free, arrive early for prime parking as the lot is small, but plenty of allowable parking a bit farther (few hundred feet) along the road. We arrived at around 11am and the parking lot was packed but we parked along the last few spots on the road (a few car spots away from the sign denoting end of allowable parking). Difficulty - Moderate for most people, easy for seasoned hikers. No surprises since the trail consists 99% of fairly boring under 45° incline to the top with plenty of gravel and small rocks lining the path. Probably super easy for experienced hikers, piece of cake since there are no scrambles or climbs. Moderately difficult for me since it felt like climbing a constant low flight of stairs. The lactic acid buildup in my calves was unbearable and warranted plenty of breaks. The roundtrip took us around 4-5 hours, plus some time for rest, picnicking, and photographs. I barely drank two bottles of water, though I prepared four just in case. Note, don't pack too heavily, as the upwards incline is much more grueling with the added weight on your back. A walking stick makes the rocky road easier to balance and gain momentum on, much recommended if you like using them. Wear thick bottomed shoes with ankle support to best traverse the rocks. Not nearly as difficult as Stairway to Heaven (aka Rocky Scramble Hell) and Surprise Lake Loop (wet rock scrambles = injury and confusing trail heads). This trail is a simple, one-way. Going down was way easier for me, especially since I ate most of my baggage. Scenery - views on the way to the top are nothing special, just trees on both sides of a straight upwards rocky gravelly path. The hotel ruins was a nice break from the trees. The hotel, mountaintop view, and fire tower made up for the work though. Wildlife - a few scuttling colorful daddy long legs, a chipmunk, a hawk/falcon swooping by for a photo of the view on top, and other cute spiders. Signs clearly warn hikers to stay on the path and beware of snakes. Ranger at the visitor center at the top of the trail also warned of rattlesnakes in the area. Cool to see some snake skins in the visitor center (and scrabble!) Landmarks - 1) Abandoned hotel ruins - halfway along the trail, super cool spots to take photos and plenty of space to do so. The remaining walls are covered in plant life and feels surreal to stand inside and imagine what it was like when the hotel was in business. Great historical spot to take a break as well. 2) Visitor center - at the top of the trail, park ranger to welcome visitors and offer free water and accept donations (sad I didn't bring any money that day). Volunteers lounge around relaxing and waiting to help out. Cute outhouse available, but too many flies personally for me. From the visitor center, go left for the fire tower and right a few minutes on the trail to the mountaintop view. 3) View from the top - beautiful span of trees and bodies of water including the Hudson as far as can be seen. Great photo opportunities and great place for lunch on the rocks. Probably what people come here to see and very much worth the climb. 4) Fire tower - abandoned years ago due to its expense (visitor center info said more people were reporting forest fires than rangers), and the structure is still up for visitors to climb. Not recommended for anyone with a fear of heights. Six rickety metal stair compartments to the top. I took it real slow and kept telling myself it was just a staircase while not looking down, not feeling the wind gently brushing the tower, and grasping onto every handhold. Saw plenty of kids go up the tower no problem. At the top, there's a small cabin with just enough room for a few people to stand and look out the windows at the world numbing view. At the base there are a few wood picnic tables perfect for lunch. Crowds - surprisingly not too crowded. Parking lot and nearby parking was full but trail is very wide and easy to avoid others. Passed maybe 20-30 people along the trial the entire time. Not too much trash spotted. As usual, please bring your trash with you and pack light if it's a problem. Worthwhile? - absolutely, even if you prefer scrambling and tricky paths, this experience is definitely one you might really really love. tl;dr gravelly incline, spectacular views, historical landmark, fire tower to climb, good parking spots, a little boring but just my kind of hiking, good picnicking read more

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It's beautiful in the winter, albeit FREEZING! It's an easy drive away from Kaaterskills Falls, and provides such a good view of the Catskills region. I'd love to hike this in the summer or fall, but winter hikers beware: wear layers, waterproof shoes, and be prepared for large gusts of cold wind! read more

Wow, I can't say enough good things about the view at the top of this hike..... It's truly breath taking. I didn't climb the fire tower, but opted instead for the scenic overlook, with amazing vistas if the Catskill Mountains and comparatively less amazing views of the Hudson River. When the Hudson River is the "bad" view you know you're in the right spot. If you are a little "Heights Sensitive" like I am, the scenic overlook point will make you a bit queasy, but there is plenty of space and room to hang out far away from the edge and still enjoy the views. The hike itself is not very interesting. It's a little bit too well trafficked for my taste, with no interesting scenery to speak of, and no wild life, aside from a few very cute chipmunks. There are multiple signs warning of rattle snakes, so I guess it's good that chipmunks were the only wild life I saw. The trail requires some huffing and puffing to get up as it is quite steep in places, ascending 1400 ft in just over 2 miles. You will sweat and you will be out of breath a bit, but the view at the top makes it worthwhile. I thought I would enjoy exploring the abandoned hotel on the trail, in fact that was what drew me to this hike, but I didn't spend too much time there as it wasn't very interesting, and apparently that is the place most of the rattle snakes in the area occupy, so the risk/reward balance didn't temp me to do much more than peak my head in a window or two. read more

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fun hike. hiking up was challenging due to the steady incline and hiking down was challenging on my knees and calves with all the rocks but overall very fun experience if ur doing it with a friend! awesome workout too. not quite muddy because it hasn't rained the day before. but the trail doesn't get much sun so if it has rain the trail will definitely be muddy and slippery. trail is mostly trees until you get to the abandon hotel which was so nice to see. fire tower was cool to climb, a little scary, windy, and cold up there but the view is worth it. scenic view was amazing as expected. picnic tables are near the fire tower for a seat and snack break. also saw so many cute dogs hiking as well :) overall was 4 hours. minus all the breaks and time spent at the top, this is a short easy hike. ~1.5 hr hike to the top is the time it took me. read more

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Amazing and beautiful! Even on a foggy day!! But you have to be in good shape it's hard to get up the hill!! Just prepare yourself it's not easy read more

Overlook Mountain - Hiking Near Me - Woodstock, New York

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I huffed and I puffed, but I made it to the top. Overlook Mountain is a great hike and an even better place to take some photos. I would rate the hike a moderate, but I could see why it would fall in to the hard category for people that aren't active hikers. That being said, I am just over 300lbs at the moment(a minuscule amount of which is muscle) and I was able to complete the hike with a lot of grumbling and sweating along the way. If you stick with it, you will make it and will be happy you did. After you are done checking out the buildings, keep going there a a fire tower too. An afternoon well spent to say the least. read more

Overlook Mountain - Hiking Near Me - Woodstock, New York

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This is a horrific hike. The top is worth it I guess, but I'll never do it again. No wonder the hotel went out of business like 17 times: no luxury accommodations on earth would be worth that climb. I love hiking. This is a 45-degree incline on a dirt road. The whole time. And bring a drone if you want to be one of a million people at the fire tower getting the most perfect views for your basic Facebook page. I have to go lay down now. read more

Hiked Overlook Mountain's fire tower trail on a Saturday afternoon in October. A moderate and relatively boring trail with a decent payoff at the peak, but found the single path up and down disappointing. Quality: Overlook Mountain is a moderate hiking trail found in the Catskills. The trail we followed culminated at a fire tower with 360 views of the surrounding area. The trail is easy to follow, but is tough on both the way up and way down because of the steepness. It is a popular trail, because its length still allows for a full journey in just a few hours. Quantity: In total the hike was about five miles, but the steepness makes the trek up longer and more challenging, though I also saw a few folks fall coming down too quickly. Value: Free to visit, with a donation box at the top. Ambiance: Overlook Mountain is located in the Catskills near Woodstock, New York. We visited the trail in autumn, which is perfect to enjoy the changing foliage. The total trip is around five miles, with the same trail used for going up and down. Towards the top you run into several abandoned buildings, a rattlesnake preserve, and the fire tower. While you don't need to climb the shaky fire tower to enjoy the views, even going a little way up offers a beautiful perspective of the area. Crowd: Since it is an up and back trail, at times the path gets busy. Lots of dogs and a surprising amount of children made up the crowds on this moderate hike. Service: On the day we visited, they had rangers at the peak with water, dog treats, and snacks. Since most people failed to bring these necessities, it was much appreciated. Parking: A small lot near the trail fills up quickly. There is an overflow lot down the road, but be careful parking along the road as they apparently ticket quickly. read more

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The best hike I've ever been on. It's relatively strenuous, as it is entirely uphill. The way up can be slightly boring, but the reward at the top is absolutely tremendous. Old ruins you can explore, a fire tower, and stunning views. It blew us away once we reached the summit. Be mindful of staying on the path, as there are rattlesnakes all over the mountain. Stick to the trail. They are also within the ruins, so watch where you step. This hike is highly, highly, recommended! read more

Good hike always! Going to the top on a cloudy day is super magical and one of the first hikes I take people on when they're new to town

Tough but rewarding hike! The view from the fire tower is gorgeous especially in fall. Friendly people and dogs along the hike. The hotel ruins were so cool to see and a good indication that you are almost to the top. I would definitely recommend! As stated by others the only problem is parking. read more

Overlook Mountain - View from the fire tower. - Hiking Near Me - Woodstock, New York

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Great hike that rewards you at the end; having said that be ready for: -a steady incline up for an hour or so, looking at practically the same view -being chased around by bugs all the time -seeing tons of chipmunks running around read more

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A perfect short hike, amazing views and a good workout. I found Overlook after a quick search for hikes in the area, I like the vicinity to the town of Woodstock with plenty of shopping, restaurants and bars. The entrance is located right across the Buddhist temple but PARKING IS AWFUL. There is a very small lot that fills up early and don't try to park on the street (unless you want a $150 ticket). Despite all the cars lined around the lot, I saw plenty of tickets around 12 on a Sunday afternoon. We were able to drive down the road a bit to find a ticket free spot to park while we hiked. I enjoy this trail because of the views, steep climb, shaded path and easy to follow. It is literally a direct path up to the top so no need for a map/worry about getting lost. There is an amazing abandoned hotel near the top (perfect for some Instagram shots) and the view at the top is worth the climb. Try to go up the water tower for an even better 360 views of the surroundings. It took us about 2 hours to go up (with waiting/climbing the water tower) and back. I have read a lot that this takes 3-5 hours, maybe we have a quick pace? Anyway, a great hike and I suggest taking some time to explore the town a bit for lunch afterwards! read more

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This was an unexpected amazing hike! Easy to get to (google the Buddhist temple across the street for an actual address for your gps), well-marked, and beyond beautiful views. The first part of the hike is straight-forward; just follow the path allllllllll the way up (don't forget to stop once in a while for water/soak in nature). Once you get to the ruins, take a few minutes to explore them. So cool. So, so, so cool. Great place for pictures, you'll definitely get some extra likes for the selfies you take here. Keep following the path and you'll come to a very well-marked trail markers (stay left for the fire tower). Keep going a little bit and boom: fire tower to your left (be mindful of the rattlesnake warnings. I didn't see any but holy crap was I mindful). I saved the fire tower for last and made a left at the ranger station (keep being mindful of those rattlers) to head for the cliffs. Holy crap. The views from the cliffs. I was in awe and spent a good 30 minutes just sitting there, snapping a few pics (gotta get those likes up), and really taking everything in. I highly recommend this hike, probably more than any other hike in the area. I'm a huge Breakneck Ridge fan but I do that one so often that I take the views there for granted. I couldn't see anyone ever taking the views from Overlook Mountain for granted. read more

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I hike the overlook mountain with friends and I really enjoyed it. It was my first hike in a VERY long time and it was worth it . Getting to the top and that magnificent view it was definitely worth the 5 mile hike. Just watch out for Timber rattlesnakes, cause they are around it, avoid going off path and everything is gonna be fine. read more

Be prepared for the altitude change and shortness of breaths. Pack light for a day hike with extra water and snacks along the way. About a 3 mile hike up and you come across a abandoned hotel that was built in the early 1900s I believe. It's a awesome place for a few decent photos but watch out for snakes! I didn't come across any but there are signs for snake warnings all over the trail. Another half mile up the trail you will be at the base of the fire tower. If you not afraid of heights I suggest you take that step t9 the top of the tower and enjoy a very scenic view along the Hudson river. Remember to look down when your at the top of the tower! Head back down the fire tower and take the other route behind the outhouse for more gorgeous views at the overlook along the cliffs. Becareful walking by the outhouse....! This outhouse is by farrrrr the most rancid smell everrrrrr. Omgggg sadly I had experienced this outhiuse first hand cause I had to use it.....and OmG it was the smelliest of all smells! Overall this is a very cool hike and awesome views! read more

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We hit this trail on what was probably the perfect day. Very low humidity, with temperatures ranging from the low 70's to high 60's, and a consistent breeze. This hike is a 5 mile loop, and on the trip up, you gain 1400 feet of elevation. You do the math. It definitely feels like a "climb" pretty much the entire way up. Walking sticks are not a bad idea (we didn't use them, but saw others doing so). The shale path was pretty smooth for the most part. Around 2 miles in, you encounter the ruins of the Overlook Mountain House- equally beautiful and creepy. You're free to roam around as much as your common sense will allow... we went down a few dubious stairwells and did a little climbing, but lived to tell the tale. Try to find the moss-filled bathtub! The first reviewer is NOT JOKING about the insects. There's definitely method to their madness. We didn't really encounter any bugs (aside from flies buzzing around on the edges of the trail) as we hoofed it up the trail, but miraculously, as soon as we saw the ruins and were eager to rest for a bit and take some photos, they launched their assault. In our ears and eyes and noses and on our clothes and in our clothes and SWEET JESUS THEY'RE IN MY HAIR. They followed us for the rest of our trip to the top. Many photos were ruined by involuntary twitching and swatting. Let our experience be a cautionary tale, as we didn't bring or wear an ounce of bug spray. It might help... The views from the fire tower at the top are stunning. We were there on a Saturday, so there were two volunteer guides at the top giving info about the mountain and surrounding areas. The guide at the top of the fire tower identified all of the mountains and bodies of water we observed, including the Ashokan Resevoir, so clean it's unfiltered and used in NYC's water supply (and we've got some damn good drinking water). BY FAR the best vista was the cliff behind the information cabin. There's a big NO CAMPING sign, but we talked to three guys who were packing up their gear after spending the night- they said watching the sun rise there was AMAZING. I'm guessing they're not lying. We didn't encounter any rattlesnakes along the trip, but several other hikers that day mentioned hearing and seeing a few, and one of the guides told us he had been monitoring two that had been hanging out at the summit all morning... They can get pretty big but have excellent camouflage, so if you don't want to get up close and personal, stay on the trail and watch where you're stepping and you should be fine. All in all, a great hike. I'm uploading a photo or two here, but additional photos from the trip can be viewed at my blog: http://sweatequalssuccess.blogspot.com/2011/06/hooooly-tight-calves-thank-you-mother.html read more

Overlook Mountain - Hiking Near Me - Woodstock, New York

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AMAZING HIKE! 1) This place has everything you need. A Buddhist Temple (at the base), fire tower, hotel ruins, and breathtaking overlook. 2) The start of the hike is somewhat bland, however, once you pass the ruins the hike get very interesting. 3) Also, come early, the parking lot gets full quickly. read more

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A solid hike with a fun reward. The trail is well maintained and is pretty wide, enough to stay 6 feet away from others despite it being a pretty popular place. It's an easy climb but a steep climb so you get a little shvitz in. Towards the end, there's an abandoned ruin of an old hotel. It's huge too and one can spend quite a bit of time exploring. The trailhead itself is just across the way from a Tibetan Buddhist monastery, a beautiful and striking building with countless prayer flags streaming across the outskirts and surrounding property. read more

Beautiful hike, love the fire tower. Great exercise and it's just absolutely beautiful. I love these mountains!

Tip: How to get here on gps? Google the Buddhist sanctuary right across from overlook. They have an address and it is much easier getting there using that. Another tip: if yore going, go as early as possible. This trail gets a lot of attraction. I went here last summer but I still think about it often. What's great about this trail is that it's relatively for people of all shapes and sizes. Being my fiancé and I aren't at the healthiest weights, it took us slightly longer because we took our time. However, after you come across the hotel, the hardest part of the trail is over. All of the sweat was completely worth it. If you are considering it, go for it! Just go early. We got there at 7 and were climbing back down by 11, in which a lot of people were there by that time. A great experience. Check out the town of Woodstock afterwords. Great people to meet and great food to eat. read more

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Holy crap. Climb the 2.5 miles to the top. The views are amazing; came here in early fall and the colors were starting to get vibrant. Amazing hotel ruins just before the fire tower (which, btw - I was too wimpy to climb up). There's a little outhouse at the top which was a nice surprise and just tons of photo ops. BUT, the hotel ruins.. I was awestruck. The photos speak for themselves! Parking in the area can get tight after lunchtime so come early. read more

tiring hike! it's pretty much uphill all the way. Climbing up the hill is quite hard if you have your camping stuff or a heavy backpack. It takes about 3 hours each way, rocky road and steep hills. Make sure you carry enough water if you're going! read more

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1. This is not an easy hike, nor is it extreme, but come mentally prepared. Based on what I read, I was not expecting this much of an uphill hike. It literally does not stop going up hill pretty much the entire hike. 2. I kept debating on whether going up or coming back down was worst and for me going down was worst because of all the rocks on the trail that didn't bother me coming up, but instead actually helped on the way up. 3. There wasn't too much mud until the very very end of the trail near the overlook point. 4. This is not a scenic hike until the very end, but it will provide some clarity and sense of escape along the way. 5. The fire tower at the end provides an amazing view. It's way higher than I expected, and it gets smaller/narrower as you go up. Do it and you won't regret it. 6. The volunteers and workers that preserve the space are so friendly. I made a donation. 7. The overlook provides one of the best views in New York hands down! It was AMAZING! I did not want to leave at all. It truly made the hike feel worth it. 8. Come prepared with the right shoes, water and gear. It's a great experience if you're prepared. Don't give up! Go! read more

Strenuous hike but the views are worth it when you get to the top. My husband and I did the hike to the fire tower. It's a pretty strenuous, straight up hill climb for most of the trail with few flat areas or places to rest. The ruins of the hotel are cool to see and take pictures in. Keep going to the top to the fire tower where you can actually climb up and see for miles. Definitely worth the hike. read more

Great spot, lots of history, great exercise. Remember, if you carry it in, carry it out. My biggest complaint is the litter left by careless, inconsiderate people. I used to hike it from town which makes it a little more challenging. I think being able to drive halfway up is diminishing accomplishment of the hike. Wear proper footwear and bring water. Oh, and there are rattlesnakes up there so be careful. I always had a snake bite kit with me when I made the trek. read more

Absolutely loved hiking here!! The abandoned hotel was a great site to see (though creepy, it's great for unique photos, hehe). The overlook is beautiful as well!! It took us about 3 hours to hike here round trip, but we did stop a lot, eat a bit, and wander off. Our dogs LOVED hiking and wandering around the whole time too, btw! read more

The trail is well marked and easy to follow. However, it is very steep making the way up and down tough if you are not an experienced hiker. It is a bit boring until you hit the ruins, but the overlook and fire tower are not too much further. On a clear day, the views at the top are totally worth the trek up in my opinion!! read more

Overlook Mountain - View from the fire tower - Hiking Near Me - Woodstock, New York

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Great hiking but as you go further up the incline becomes steeper. Once you get to the top there are a pleather of things to do. The haunted and enchanting hotel ruins are fascinating. Only a few minutes more you can get to the fire tower, hang in there an go see the view! Reminders: bring drinks and pack bug spray to use throughout the hike! A walking stick, along with some good walking/hiking shoes will help. I wish they would consider posting mileage markers, installing a few benches, and historical markers! The best idea from my 8 year old friend is having ATV's to take you up! read more

Amazing, nothing short of a must see, must do. As you've likely read-be prepared for a 2.5 mile hike UP, with minimal plateaus. But it's well worth the effort and evenly mixed with shade/sun. The vistas at the top, from the cliff are breathtaking. But for me, the fire tower made me a bit queasy. read more

Overlook Mountain - On a clear day you can see...well, for many miles. I see the Hudson River, the Gunks, Berkshires and more - Hiking Near Me - Woodstock, New York

There is no question that this hike is worth every step along the seemingly never ending way up. If it's you're first time climbing Overlook Mountain you will probably question yourself on the way up, wondering if it will be worth it because it literally seems like you are climbing forever, waiting for a pay off. Along this rocky, gravel path there is plenty of foliage and rock formations to admire while you mildly chastise your partner for bringing you on this uphill battle of will, but you will apologize later. Your first pay off comes when you get to the abandoned hotel - two buildings left to rot, but instead of have become an architectural playground for nature. Although they have now added No Trespassing signs, it is fairly safe to get close to and on the buildings to get some interesting photographs of nature attempting to fully envelop this abandoned relic. This is also a welcome sight because it proves to you that there are good things to come on this hike. You still have a ways to go from here. Your next pay off comes as you start to see the view through the trees on your way up to the Fire Tower. You can tell it is going to be amazing, but your view is still masked by all of the trees and rocks on your climb. The Fire Tower will let you climb even higher into the sky and see views you have probably only dreamed of. If you are scared of heights, this freestanding metal contraption will test your will as it wiggles as you walk and doesn't accept wind without a little resistance. I am afraid of heights, but I climbed this thing anyway (holding on at each level like an eagle to its prey) and it was worth it. The views will captivate you and you have panorama capabilities, this is a great spot to use it. You are close to the summit from here and you will be charged up to get there as that view is unobstructed by a tower. On you go, you are close. Some people stop here, but you have to go behind the little house and on to the peak to get what you climbed all this way for. The pay off is a majestic and endless view, one you may never see unless you are a climber. There is a small set of rocks to rest on and just admire nature and what it is offering you on this ledge. You will now feel bad for cursing your partner twice on the way up and claiming it will never be worth it because you now know it is. It's as serene a setting as it can be when you are top - sit back, relax and enjoy it. I didn't see any snakes or bears on my trip, but it is clear that they make this mountain home. The bugs were annoying, but if you keep moving you will be in much better shape. It seemed every time we stopped to photograph something, they swarmed. This is definitely an intermediate hike and although coming down takes less time, it is not much easier than going up, especially on your knees. If you don't enjoy nature, views and working to get to a destination, stay at home and let your friend or partner who does, enjoy it on their own so you don't ruin what can be a truly magical experience. read more

Overlook Mountain - From the very top. - Hiking Near Me - Woodstock, New York

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Nothing to add to the well-written (and accurate) posts but I find it disheartening that the town of Woodstock has been aware of the parking/parking fine situation for some time. Yet nothing has been done. When we spoke to a nice woman at the police station (as we turned in our fine), she clearly had heard it all before. And yes she sympathized, but it was apparently a NY State situation that they had little control over since its a NY State park (yet they collect the fines?). The funny thing is that where we were forced to park (what, we're going to simply turn around the car and go home?) required a long steep walk up to the trailhead - - harder than the trail itself! And we (and the other 50 cars) were all safely pulled off to the side. We weren't blocking any potential emergency vehicle situation. I can only conclude this is a (unkind) way for Woodstock to fund its city. Not a very hospitable way to treat visitors. read more

The main reason, I was told, to hike this trail is the pay off at the top. But for a nature-starved urban dweller who hasn't done much in the way of hiking all year, the wide, light gravel fire road that takes you to the top of Overlook offered a great warm-up to getting back into hiking mode with a minimum of discomfort. Will you huff and puff, walking straight upwards for almost the entire first half of the hike, wondering how it is that people voluntarily chose to do the Stairmaster at the gym as their primary form of exercise? Yes, you will. But unlike many steep vertical hikes, this one requires no special gear, no picking your way through rock formations and slippery leaves, and even though it had rained steadily the entire day before my hike, the gravel trail was mostly dry. Since I did the hike during the peak of fall foliage season, I would say the views and general atmosphere were pleasant - little burbling brooks, brilliantly colored leaves rustling about, and clean, crisp blue skies with views of mountain ranges behind you as you climb. The ruins of the Overlook Mountain House are fun to climb through as you try to envision what it may have looked like when it was completed (though historical accounts are vague about whether it was ever built out and decorated on the inside). This, however, just doesn't compare to the wide-open, spectacular vista that awaits at the top of the Overlook. I skipped the tower and went to the ledge, and just stood for a long time gazing out at the numerous mountain ranges and bodies of water spanning New York State and Massachusetts. It is simply natural beauty at its absolute finest, and if you're one for communing with nature, this would be the place to do it. Do bring warmer clothes for the top. Though I was fine wearing a thin, long-sleeved t-shirt on the way up, once at the Overlook I layered on a sweater, windbreaker, winter hat and knit gloves, as it was very windy. These came in handy for the walk down, which was a breeze compared to the way up. I'd rate this an intermediate hike because of the steepness of the ascent, but the distance and ease of walking make for a nice jaunt that can be done in less than 2 hours. read more