12 Mondays at Windham
Learning new lessons while revisiting an old favorite.
No matter how much we’ve wandered, chasing bigger and ever more challenging lines, we all have that one mountain that’s earned room in our hearts because that’s where we learned how to begin putting it all together. A special place where it all clicked. For me, that ski area is Windham. It was just six years ago when my wife took me skiing for the first time. It was a warm and slushy spring weekend at Hunter Mountain. The slopes were crowded and my rental boots hurt like hell. I spent two days falling on my face, but I learned how to make serviceable turns and I was hooked. There was no turning back.
I wanted moreand when winter came back around, I had a plan: I would use my Mondays. At the time, I was working as a restaurant manager in Manhattan and I had Mondays off, so I decided to spend them learning how to ski. I chose Windham because of its proximity and abundance of long intermediate trails. I wanted to ski blues and get better.
Armed with only my weekday off and a YouTube ski school crash course by Elate Media (a fantastic online video series that is best used in conjunction with on-mountain lessons which, I realize in retrospect, I should have taken earlier), I spent the next three months’ worth of Mondays teaching myself how to ski. By the end of the season, I was able to ski every trail on the mountain, and my progress had everything to do with my willingness to put in the time necessary to constantly reinforce the new skills I was learning.
You can spend a decade skiing two weekends a year and never progress past the blue trails, because real improvement requires instruction and practice. Linking your first series of wedge turns is fun, but learning how to confidently bash down a long field of spring corn moguls is even more fun, and it takes work to get there. Everyone needs a Windham—a mountain where they can learn and progress—and some time devoted to getting intimate with it.
Since that first full season, I’ve skied more than 170 days at over fifty mountains across the Northeast, the mountain west and Canada. Windham may not be the tallest, the steepest, or the snowiest ski resort I’ve visited, but it’s a fantastic all-around option within a day trip’s distance of New York City, and it’s particularly special to me because it’s where I learned how to ski.
I was excited to revisit my old stomping grounds on a recent sunny March Monday when I returned to Windham along with Nate, a college buddy of mine who recently returned to skiing after a ten-year hiatus. After a notoriously icy reintroduction to skiing at a frigid, unedgeable Jay Peak on New Year’s Eve, Nate was courageous enough to give it another go, and I wanted to find someplace to help ease him back into his old muscle memories. We were looking for a relaxed day on the slopes with plenty of blue and black groomers and good snow quality within two hours of my house—Windham checked all of the boxes.
Driving up the Thruway then onto Route 23, I was immediately brought back to my old commute. It’s a picturesque drive, full of winding Catskills country roads and epic, ridge-side vistas. We parked in the lot up near the base, which you can do for free on Mondays if you get there in time, and booted up in that lodge that had come to feel like home to me.
We began with a run down Upper Whistler, a mellow blue groomer which was covered with soft, smooth corduroy that glistened in the morning sun. The first time I skied Upper Whistler, it felt menacingly steep and I questioned whether it should in fact be classified as a black diamond. I remember desperately pole planting on the wrong side of my body, hurling myself awkwardly into each turn, determined to survive my way down the slope.
Now, five years later, I experienced Whistler as a gentle, wide, moderately pitched blue run that’s perfect for practicing long carves, short slashes, and everything in between.
We colored in the lines on Wraparound, Warpath, and Windfall, then we headed into the Wilderness Bowl area to explore Windham’s newest trails. Wolf’s Prey and Wildcat, both rated blue-black, are steep, winding trails that swoop downwards through the woods between the resort’s eastern and western peaks. Thanks to the required traverse to reach these two trails, they were relatively untracked and the snow was smooth and consistent. Somewhat tighter and steeper than the rest of the trails on this side of Windham, these would have given me pause during that first year, but they gave me nothing but joy this time.
Next we explored the steeper slopes of Why Not and Wing’n It, two fall-line black diamond trails that were, five years ago, my first foray into black-diamond terrain. I remember getting amped up to the tune of Black Sabbath’s “End of the Beginning,” cresting the headwall of Why Not just as Tony Iommi’s aggressive guitar riffs kicked in, propelling me through the next turns down the steep pitch.
I also remember face-planting here after being hurled forward by wet manmade snow resulting in a face-first slide down the headwall – the gaping smile on my face concealed by mouthfuls of snow.
The surface was just beginning to yield to the warm spring sun, covering the slopes with soft, carveable corn snow. Only Wicked was left unskied, it’s ungroomed slopes still covered in an icy film that shined in the sun and refused to soften like its neighbors.
A trip down World Cup, the resort’s original blue-black trail that drops into the Wilderness Bowl, led us back to the west side where we took a break for a beer and a snack in the sun. While a piece of me dreads the end of winter and the long, snowless summer ahead, the first kiss of the warm spring sun has a unique ability to lift the spirits, and the two months of spring skiing ahead are always one of my favorite times of year.
After our break, we closed out the day by skiing Upper Wolverine and Wedel, two double-black diamond trails that, along with Upper Wheelchair, boast the steepest pitches at Windham. The first time I skied Upper Wolverine I remember feeling like I was looking over the edge of Everest, watching the winter wind swirl the snow into the air just above the trail. It felt impossibly steep.
I thought back to my first powder day – which I also had at Windham – prior to my days of obsessively checking weather reports and forecast models. I was surprised by eight inches of snow that fell during the day, transforming the steep, often icy headwalls into suddenly-manageable playgrounds coated in soft, ankle-deep hero snow.
While I do still consider these trails to be steep, they are no longer intimidating, and I enjoyed skiing them with some style, bouncing around the soft moguls that had begun to form. I would have struggled in the same conditions just a few years ago, but what was once scary is now fun, and the trails I once skied to push my limits is are now venues to home my style and technique. It’s not that I’ve progressed past Windham—rather I am able to explore its terrain from a new angle now. Where there once was terror, there’s now an opportunity to practice side hits, or skiing switch, or launching off soft bumps. The mountain is the same; I’m just using it differently.
While it’s rewarding (and important) to push myself to improve on challenging terrain, it was equally satisfying to return to trails that I once found challenging and to witness the progress I’ve made since those first twelve Mondays at Windham. It was also a great mountain for Nate to ski on terrain that helped rebuild his confidence much the same way it had helped build my confidence when I was first starting.
It’s my 13th Monday at Windham, and I’ve realized the mountain still has a lot to teach me.