While the Vassar Farm is a beautiful place to take a walk, it’s mostly flat. It’s a totally natural human desire to occasionally feel a burning desire to go climb a mountain.
Although there’s an abundance of mountains in the Hudson Valley, one of the best places to take a hike is definitely Overlook Mountain, one of the southernmost members of the Catskill Mountains.
The trail up the mountain is a pleasant 2.4 miles from the start to the peak. The trail has found its way onto lists of trails with the best or most scenic views within the Hudson Valley. The path is about as wide as a one-lane road, and is kept well-maintained and free of branches and leaves.
A beautiful New York forest surrounds the path on both sides, and in the fall and spring, the foliage can be quite stunning. Nature enthusiasts will be pleased to find oaks, firs and spruces all along the mountain.
Overlook Mountain is a fairly well-known trail, and it isn’t unusual to run into a few fellow hikers along your way to the top.
Although it is extremely well-kept, the trail has a habit of being practically flat for several yards before launching itself into a steep slope that seemed way shorter at the bottom than it did halfway up. From the start of the trail to the peak, you will have climbed about 1400 feet in total.
Don’t be discouraged, though. Signs at the trail’s mouth list it as an “Intermediate” difficulty hike. There aren’t any sections of tough terrain or big slopes of rocks to clamber over. Even beginners who have a good level of physical fitness should find the trail a good challenge. Fortunately, the slope’s aren’t overly severe or unnecessarily long, but after a few rounds of climbing one only to find another slope a few yards ahead, you might start to question your impulse to go on this hike.
The tedium of the climbing doesn’t go on for that long though as, depending on your pace, you should get close to the top in roughly 45 minutes. And the top is where the really fun part of the hike lies.
Sometime in the mid 1800’s, the Overlook Mountain House was opened to guests of the mountain. Able to house almost 300 guests, the hotel burned down several times before it finally closed in 1940.
Before that, though, the House definitely played host to an Agatha Christie-inspired murder-mystery. The ruins of the hotel are right next to the trail not far from the mountain’s peak and can be explored, if you so desire.
Although since everything but the stonework has long rotted away so it looks more like a Roman ruin than a former hotel, you can still tell where the various staircases and rooms were located.
If you do chose to venture through the hotel’s ruins, make sure to watch your step. Some of the staircases and windows that originally opened onto rooms on the hotel’s second floor now open onto thin air.
A short distance further up the trail is one of only a handful of fire towers still remaining in the Catskill Mountains. At its feet are a handful of picnic tables and a small log cabin.
Here at the top you will probably find some of the other hikers you may or may not have encountered earlier on stopping to rest or eating a family picnic at the tables. During the summer, there is usually a steward staying in the cabin who serves as caretaker of the peak.
The fire tower can be climbed all the way to the top. While it can get a bit windy at times, the tower is made of steel and it is quite sturdy.
The tower is only about 60 feet tall and it was renovated late in the 1990’s. From the top, you can catch a fantastic view of the entire Hudson Valley and the rest of the Catskills.
Down a nearby bend in the path is a small outcropping of rock just above the tree line which allows a sweeping vista of the Hudson River meandering its way through the valley.
Sheltered from the wind by the mountain behind it, the outcrop is calm, quiet and sunny.
If you’re lucky enough to be with someone else who shares your hankering for a good hike, this is the perfect place to just sit down and appreciate the view. You could join the dozens of other people who have carved their names into the stone, some as old as the 1850’s. The outcrop is also perfect for deep musings on the meaning of life or whether or not the squirrels at Vassar are really deceased English majors.
Though you might have flashbacks to the horror of the long stretches of steep slopes, you’ll find the way down to be even more pleasant than the way up.
By the time you get back to your car in the parking lot of the Buddhist temple at the trail’s start, your legs will be fully recovered and you’ll be looking forward to the next time you can go on a hike.
Speaking of, you will probably need to convince someone with a car to go with you (unless you have one of your own), since Overlook is just outside of Woodstock, New York at the top of Meads Mountain Road.
You should plan for a hike to take a whole afternoon, as Woodstock is about an hour away from Vassar, which is perfect for a Sunday afternoon study break with your friends before the weather gets too cold to go outdoors,
You could also take a detour and visit the town of Woodstock itself. Another option is to check out the various mansions and estates along the Hudson River on the way back to Vassar.