Overlook Mountain Trailhead
This is one of Woodstock’s most popular hikes, and with good reason! It offers an incredible view looking down into the Woodstock area and surrounding towns / woodland, and an opportunity to explore the ruins of an old Catskills hotel. You can also choose to take a longer hike to Echo Lake, which is unique as the lake is only accessible by foot, making it somewhat of a hidden gem / off the beaten path destination! 4.6 miles out and back, moderate difficulty.
This hike is the shortest yet most difficult / steepest way to get up to the top of Hunter Mountain, which is the second highest mountains in all of the Catskills! If you decide to take this route of seeing the Catskills from one of the highest perspectives, you will climb 2000 feet in only about 1.7 miles! The entire hike is primarily wooded, with stellar views coming through as you begin to reach the top! If hiking during the winter, you must bring crampons / spikes!
Located near Overlook Mountain, this far more condescend hike crosses over into the surrounding forest area, allowing you to experience streams, a nearby lake, and mossy surroundings with slight elevation changes all while keeping it short and sweet. Experience so much of what makes the Catskills beautiful without consuming the whole day at one location! It is also located very close to the beloved Buddhist Monastery, which is frequently open to the public for meditations, sound baths, readings, and so on!
Catskills Thorn Preserve
Another beautiful walking destination! A sunset during a night of your stay here is not to be missed. The property is a large field facing a gorgeous and vast mountain view that is visible for the entire walk. The paths lead one through a bit of a winding, maze-like pattern, and depending on the season you are visiting, you might be lucky to see what biodiversity the Catskills truly have to offer! Occasionally, the educational center on-site will lead botanical / nature walks to help visitors identify the special flowers, herbs, and plants that keep the preserve so vibrant!
Giant Ledge / Slide Mountain
There are multiple routes that you can take for this hike that cause the length and difficulty to vary. Overall, it is a moderately difficult hike in the sense that parts are very steep. This does not mean you have to be a hiking expert at all – more so just that you have the endurance / breath to be able to navigate some difficult spots! This mountain sits atop a 375 year old meteorite hit, and offers so many beautiful surprises in the natural landscaping. Some views from the ledges are so panoramic that it actually feels like your eyes physically cannot take in the entire view at once! It’s truly magical, vast, and diverse.
This hike is considered very simple and easy-going. It is located near the center of Woodstock’s village – park here for a pre-dinner walk and then head to dinner at our town favorite, Silvia, or enjoy vegan fare at The Garden Cafe. It is more of a walk than a full-on hike in terms of length / difficulty, but being that it is through a beautifully wooded forest area, you get all of the perks of some of the lengthier, arduous area hikes, but in a condensed timeframe. It takes about 35 minutes to walk the trail, and you will pass beautiful streams, fields, and occasionally, dogs and their loving owners!
Mount Tremper Fire Tower
If you hiked Overlook out of a love for fire towers / an even more elevated and dramatic view at the peak of your hikes, this lesser known hike is a must. This is definitely a winter favorite. With certain areas that feel more pine-centric / green and then others that are rockier / full of oaks and maples, you really see quite the variety as you ascend closer and closer to the peak. The fire tower at the top of the hike is extremely rewarding – you almost feel as if you’re in a small plane once you’re up there because of how far you truly climbed up the side of this hidden treasure! 5.9 miles out and back, relatively difficult but not too demanding overall.
This hike is located right outside of the town of Phoenicia. We recommend parking in the town itself and walking to the trailhead, located at the village’s park / recreational field. This hike is different because while we often come to the Catskills to see the best, most unadultured natural landscapes, it can be cool to see a town from so high up (At one of the major viewing points overlooking the ledge, you will be able to see all of Phoenicia / tiny cars driving through the seemingly miniscule town). Don’t be fooled though – not only will you be hiking through the side of a mountain, but you will be able to see the mountains that envelope the town of Phoenicia on either side as you make your way through the hike. 2.1 mile loop!
This is another hike that we love for the excellent ledge-side views that it offers of the endless forests below… It is relatively short but not too fleeting. The hike is about 4.98 miles total, but one can reach some of the best views about halfway through the hike and feel satisfied. From one of the ledges along the trail, you will be looking across the way to yet another mountain towering over the same forest, which is quite the surreal experience! It is located off Platte Clove road, which is closed November-April. If you would like to hike this route in the winter, you musty park at the top of bottom of the road in wither Saugerties or Elka Park and walk by foot down the seasonally-operated road. When travelling on this road by car, drive slow and take caution as there are major drop offs and it is extremely narrow, making it prone to accidents if one is not paying special attention to the rugged circumstances.