I’ve hiked Windham High Peak, the northern-most Catskill High Peak, once before. It was on a gorgeous, sunny summer day in May 2017 after having just completed my Real Property final during my first year of law school. I set off by myself and traveled in my car a little over an hour southwest of Albany to hike this 3,524 foot mountain.
There was nothing particularly eventful about this 6.6 mile roundtrip hike, but I do remember having a wonderful time and remarking to myself how I’d love to return to Windham High Peak someday to hike it again, though ideally with a hiking buddy to keep my company. Fast forward two years later, I fulfilled my promise of returning back to Windham High Peak and this time I brought a close friend of mine, Katie, with me. However, the trail conditions I experienced during my first hike of Windham High Peak were nothing like Katie and I would encounter on Sunday, June 16th, 2019.

Blackhead Mountain Range, taken May 2017 – Photo Justin Devendorf
Everybody needs a break
Currently, I am studying for the Uniform Bar Examination (“Bar Exam”) following my graduation from Albany Law School a few weeks ago. I have worked extremely hard over the past three years of law school, and it has by no means been easy. I have relied on hiking as a way to, in so few words, “put my mind at ease,” in a high stress environment such as law school.
Self-care, regardless of whatever career one decides to enter, is incredibly important.
Self-care, regardless of whatever career one decides to enter, is incredibly important; Everybody needs a break, everybody needs a way to be able to relax. It not only makes us happier, healthier people but also is necessary to make us as productive and successful as possible at our jobs.
To that end, I’ve been pulling eight to ten hours of studying per day, six days a week for the Bar Exam since the end of May. This is not uncommon (and I’m not looking for sympathy whatsoever) because I know that this is what I must do in order to pass the Bar Exam. But like I said above, “Everybody needs a break,” and on my one day-off a week that I give myself, I decided that I wanted to go for a hike. Lucky for me, Katie was more than happy and willing to go on a hike with me when we both had time off, which happened to be Sunday, June 16th. With our plan set, we set off from my apartment building just after 7:00am and made the drive to Windham High Peak.
Rain, rain go away!
Prior to leaving on our hike of Windham High Peak, I checked the weather forecast (as all hikers should do) and the forecast did call for scattered rain throughout most of the day, with heavy rain forecast for the early afternoon. Now, I’m not opposed to hiking in the rain so long as one is properly prepared and there are not thunderstorms in the forecast.
That being said, I would be lying if I said I enjoy hiking in the rain, because I do not. Neither does Katie, however, when we arrived at the Windham High Peak trailhead at the Elm Ridge Parking Area it was not raining. But, we were prepared for the elements regardless and set off on our journey after we signed our names in the booklet found at the trailhead (Again, like all hikers should do).
One thing I noticed almost immediately was that there were several other trails that branched off of the main Escarpment trail that Katie and I followed to get to the summit which hikers could explore as well. We didn’t go down any of those trails, but I do believe “The more places to explore, the better!” so it was nice to see that if hikers did not want to go to the summit of Windham there were other options for them.
Katie and I didn’t let the rain ruin our hiking experience.
About a mile into the hike, the rain began. It started off slow, and Katie and I were in an area of the forest provided excellent cover from the rain, so at first we did not get soaked. This would change as we further ascended the mountain, and the tree coverage would not completely save us from becoming wet. Katie and I didn’t let the rain ruin our hiking experience, though I did say to myself several times “Rain, rain go away!” but to no avail.
Admiring the Wildlife of Windham
Katie and I continued our trek up Windham, partially soaked, somewhat sore but undeterred in our quest to reach the summit. Another aspect of hiking I enjoy is seeing the wildlife that inhabit the wilderness. No matter how big or small, I find all natural life to be fascinating. One common woodland critter I see frequently is the small, Eastern (red-spotted) Newt.
According to the New York State Department of Environmental Conservation, this member of the salamander family is commonly found throughout New York State and the Eastern United States. Averaging about three to five inches in length, they can be easy to miss by hikers, but they are still nevertheless an important part of their ecosystem.

I pointed out our tiny friend to Katie, who also enjoyed seeing what I found. I took a quick photo and Katie and I went on our way, but not before seeing another three to four other salamanders during our ascent and descent of Windham. Katie and I remarked to one another that perhaps these salamanders enjoyed the rain, unlike Katie and I, who were progressively getting more soaked.
Reaching the Summit
After just under two hours of hiking through a wet, muddy and at times somewhat steep terrain, Katie and I made it to the summit of Windham High Peak. The summit is covered by trees and relatively flat, however, the views of the Blackhead Mountains to the south are gorgeous. Well, the views of the Blackhead Mountains would have been gorgeous had the clouds not obscured their view.

Photo – Justin Devendorf
Katie and I found some cover underneath a large pine tree and ate some light snacks, drank some water and rested up. We were both very proud of what we had accomplished, even if the weather was not so nice and even if we did not get to see a great view from the summit. Why? In my personal view, experiencing the outdoors is not always about the “great views,” that await one at the summit or being able to hike in comfortable weather. While those aspects of hiking are completely valid, there are other aspects of hiking that sometimes force people outside their comfort zones yet provide them with memories they will nevertheless cherish.
It was so nice to be able to not have to worry about the Bar Exam for a few hours.
For me, it was so nice to be able to not have to worry about the Bar Exam for a few hours; to not have to worry about the stresses that come with life and to just, even if I was soaking wet and muddy, enjoy the simplicity of walking through the woods and hiking a mountain with a close friend. That, is what I will remember about my second hike up Windham High Peak.

Trip Report
Lessons Learned
Always check the weather forecast and be prepared if the forecast calls for rain. That does not mean one should not go hiking, but extra preparation is always needed in such conditions.
Book Recommendations
Favorite Gear Used
- My light, black rain jacket
Gear They Wish They Brought
- My trekking poles because some parts of the terrain, especially near the summit, were very muddy and I was slipping because of the rain.
Favorite Meal or Snack
- Almonds! My favorite hiking snack because they are light, easy to pack and high in protein.
Maps, Routes and GPS Information
Route Statistics: 6.84 mi, 1,838′ elevation

Caltop Map: https://caltopo.com/m/K71E