I’m a creature of distinct habits, most of which make little sense to the rest of the population—like starting my day at 5:30 a.m.—but are strangely comforting to me (potato, potatoh). Among these is a summer schedule of regular walks, typically four to six miles, to begin the workday. Not only do these jaunts give me a chance to get outside, get moving, and work out those mysterious “sleep injuries”—groaning muscles, tendons, and joints that woke up this way—but they also give me a long, uninterrupted stretch of mind clearing, not to mention escape from my home office. So when an extended busy work period from April through June, followed by a week of 90-plus degree temperatures, kept me from going outside for more than 30 minutes at a time, I started to get a little stir crazy. The solution: a hike on Overlook Mountain in Woodstock, New York.

I chose Woodstock for a couple of reasons. My husband was on vacation that week and we agreed to take a day trip to a city or town with a mixture of outdoorsy and indoorsy things to do. It also happens to be an easy drive—about an hour and a half door to trail—and doesn’t involve sitting in traffic on a car-clogged highway. Also, online research told me Woodstock had lots of good restaurants, an important consideration for a person who grazes every few hours and needs instant refueling after a big excursion. Finally, Woodstock has a variety of hiking trails to choose from, including Overlook Mountain—home to quiet, shaded woods, haunting ruins, and stunning panoramic views at about 3,100 feet.

Since I’m currently working with a torn meniscus, I wanted to know what I was in for with a hike on Overlook Mountain, in terms of distance, elevation gain, and overall difficulty of the trail. I found a variety of conflicting opinions on different sites, with some folks (most likely the young and/or in great cardiovascular shape) classifying the 2.5 mile out-and-back trail as an “easy walk,” some calling it moderate, and some insisting that it was quite difficult. Admittedly, the 1,370-foot elevation gain gave me pause; though I work out five times a week and teach yoga class once a week, I dislike extended cardio workouts, and steep inclines are not my friend. Especially not on a whiny knee.

But then I saw the photos of kids—and I mean little kids—hiking the trail with their parents, and I thought, If a six-year-old can do it, I can suck up little discomfort. And while I was looking forward to the views at the summit, Overlook Mountain has an additional draw for me: the ruins of the Overlook Mountain House.

To put it politely, I’m an archaeology nerd. Abandoned Victorian train stations? Here I come. Medieval Spanish castles crumbling into the Mediterranean? I’m there. The remnants of human ambition, rising up out of the forest like mildewed apparitions? Let me at ’em. The deal was sealed.

I’d read that Overlook Mountain Trail can get cluttered with tourists on weekends and weekday afternoons, so we chose a Monday for our trip. We got to the trailhead fairly early, about 9:30 a.m. It took a little time to apply sunscreen and insect repellent—the latter, in particular, is a must, as the bugs can be brutal in these woods—and then we were off.

It took only about a half mile of traveling steadily uphill before I started to get winded and my knee began misbehaving like a brat kicking an airplane seat. In my defense, most of that 1,370-foot elevation gain takes place in the first 1.5 miles of the trail. Not so much in my defense, the a hike on Overlook Mountain Trail is, in reality, not that hard. True, the steepness of the first part is a challenge if you’re not someone who runs or hikes regularly, but the trail is wide, nicely maintained, and fairly even. There are a few parts, especially toward the top and bottom, where the loose stones make footing tricky, but on a dry day, these aren’t too much of a hassle.

I’d read that there were wild raspberries along the trail, but none had ripened by the time of our visit in early July. And while there are signs posted at the top and bottom of the trail warning of timber rattlesnakes, we saw nothing more exotic than a chipmunk sitting on a stump, nibbling at something that appeared to be small, floppy . . . and hairy. Go figure.

Right about at the 2-mile mark, the trail comes to an abrupt stop at the base of a set of stairs leading up to the Overlook Mountain House. Rising up out of the forest like a concrete skeleton, complete with gaping “eyes” and “mouth,” the remnants of the hotel stand tall, imposing, and somber, a reminder of the Catskills’ popularity with the affluent set starting in the early to mid-1800s. By the 1940s, most of the historic resorts were finally closed for good—and subsequently demolished, some consigned to trash heaps and others salvaged for scrap.

What you’re looking at is actually the burned-out structure of the third hotel built on the site. The first, a smaller wooden lodge, was built in 1833 and closed a few years later, when the owner realized how difficult it was to lure tourists on top of a mountain without train service or other practical means of transportation. In 1871, the new owner tore down the original building and created a 300-room hotel on the site; it burned down just four years later. A pair of brothers rebuilt the hotel in 1878, but with business still limping along, they sold it to New York City hotel magnate Morris Newgold in 1917. The building promptly burned down again in 1921.

Undeterred, Newgold rebuilt again, this time in fire-resistant concrete. Though he had big plans to expand his mountaintop empire, he didn’t have the cash to back them up, and in 1940 sold the property to the state of New York. The abandoned hotel stood until 1970, when a third fire wiped out all but the concrete structure of the main building and smaller edifice—lead window frames frozen open by time and rust—behind it.

After a few minutes’ exploration of both buildings—you can walk through them, but proceed with caution, as some areas are in greater disrepair than others—we continued up the path to the summit. In a half mile, we came to a small red building with a sign pointing in one direction for views and the other for the fire tower. By the sound of it, a group of small kids and their moms had headed out to the overlook, so we trekked over to the fire tower.

The tower’s stairs are steep and angled downward, so hanging on to the handrails is a must for getting up all 60 feet to the top. While the observation room at the top was chained shut, we still got plenty of phenomenal views just from turning around on the uppermost platform—the Hudson River in one direction, the Westkill Mountains in another, and the Ashokan Reservoir in yet another. The breeze at the top also felt pretty amazing after the sweaty hike up the trail, so I was more than happy to pause and take it all in.

We descended the fire tower and walked across the way to the overlook, and the views here are no less stunning, if not 360 degree. I wished I’d brought a lunch, because the flat rocks at the summit are perfect for a rest and a picnic. Instead I contented myself with taking a load off and snapping a few pictures in each direction.

With our stomachs rumbling and trail traffic picking up, we headed back down the mountain. The great news? The first mile and half of the descent, with the exception of a passage near the top that has lots of loose rocks, are super easy going, and you can pick up some speed here.

The not-so-awesome news: what comes after will make tired legs and injured knees beg for mercy. The last mile is steep, with very few areas that level out to afford a rest, and the uneven ground and loose rocks make traversing difficult. And with lots of hikers coming up the trail, you’re pretty much forced to walk a straight line for much of the final passage down. Walking poles will help, if you’ve got them. Otherwise, shift your weight back, pick your way carefully downhill, and think happy thoughts of wherever you’re going afterward for lunch or a snack. At least, that’s what works for me.

The hike on Overlook Mountain—including wandering through the crumbling remains of Overlook Mountain House—was a fun break from the usual view from my home office window, and worthwhile way to spend a few hours on a weekday morning. If I lived closer, I’d probably go back again. For now, I’ll to content myself with hikes on local trails with interesting ruins, like Shaker Mountain in Hancock, Massachusetts, to get my fix of natural wonder and human folly.