I made it back to a 4000-footer Friday! And if memory serves, it’s the first time I’ve climbed one alone since writing 4000s by 40. I’ve returned to the 4000-footers often since publishing, but always with friends or family. It was a funny feeling being back for a solo run—it really reconnected me with the experiences from the book, since most of those climbs I did by myself.
I still frequently hike alone, but when doing so, I usually choose something smaller. Lately I’ve been doing the 52 With A View (52 WAV) list, and that’s actually what brought me back to a 4000-footer this time. Namely, Mount Jackson.
Mount Webster is one of the tallest on the 52 WAV, at 3,910 feet, and I figured with Jackson being right next door, and only a little over one hundred feet higher, what the hell—let’s make it a loop day of some big guys.
Looking down from the summit of Mount Webster.
Mount Webster
First up was Mount Webster, which I had never climbed before. The trail has plenty of roots, rocks, and steep parts, but what I love about the Webster-Jackson trail in general is that there is always a good soft spot between the rocks and roots to plant your feet. Your legs don’t take the pounding they do on rockier mountains like Madison or Lafayette.
There is a fork in the trail, a little over a mile of the way up, where you decide whether to climb Webster or Jackson first. Shortly after opting for Webster, I came across the Silver Cascade Pool. Usually, water flows pretty well here, but with so little rain this summer, there wasn’t much cascading going on.
The total distance to the summit is about 2.5 miles, and going at a moderate pace for me, I was there in about an hour and forty-five minutes. If you’re with kids, be careful not to let them get too far ahead, as there are some really steep drop-offs here. Almost the moment you emerge on the summit, you come to the edge of a cliff. But what you get to see is so worth it. The sky opens up, and looking across the notch you get a beautiful panorama of Willey, Field, and Tom.
From left to right, three 4000-footers: Mount Willey, Mount Field, and Mount Tom
Wrong-Way Matt
I know I call this website wandering matt, which I adopted from my Instagram handle when I first started sharing pictures and stories of some adventures, but I’m starting to think I need a new site name. Wrong-Way Matt seems fitting, because more often than not, I seem to take a wrong turn on a trail wherever I go. Even on a supposedly straightforward one like the Webster-Jackson loop, I took at least three.
The first mistake came when I was ascending. There was a patch of pine needles that looked so intentional and soft, I assumed it was the trail. A few minutes into that, I realized my error. The second mistake happened here, when I was standing on the summit of Webster.
Maybe it was the view, but I couldn’t help but venture this way at first.
The Webster-Cliff Trail
Trailing along the ridge, I mistakenly believed that the Webster-Cliff Trail was in fact the Webster-Jackson Trail, and that I was about to begin my loop to Jackson. I don’t know why I thought that because it didn’t make directional sense, but maybe my mind was tired from the climb up. I ended up descending a good chunk of the Webster-Cliff Trail, probably for about twenty minutes, before I realized something was off. The trail I was supposed to be on was the AT (Appalachian Trail), and I kept thinking to myself that this was a cruel path to subject thru-hikers to after having hiked all the way from Georgia. But it wasn’t the AT, of course. I’m just an idiot.
On the plus side, this section of the Webster-Cliff Trail is STUNNING. Looking out on the notch, you get views of the Willey House site and a broad scope of the White Mountains. It was worth every second of the error.
I loved this view looking down the Webster-Cliff Trail.
Mount Jackson
When I finally got my internal compass corrected, I made my way towards the planned destination of Jackson. At first, I thought my error on the Webster-Cliff Trail would have cost me too much energy, but the mile or so over from Webster to Jackson isn’t too bad because it’s a very slight incline. Jackson stands at 4,052 feet, so it’s not terribly steep over that stretch.
At the summit, I met a lady feeding gray jays, and I had a friendly stop with her to watch and converse. After departing, I made my third mistake of the day and ended up back on the Webster-Cliff Trail again. It just wouldn’t stop messing with me! Fortunately, I had downloaded a couple of GPS tracks from other hikers on Peakbagger.com, and when I double-checked those, they brought me back to where I needed to be. That goof probably cost me another twenty minutes of unnecessary hiking.
Summit of Mount Jackson
Together Again
My big takeaway from the hike is that some places never get old. I don’t know how many times I’ve climbed Jackson, but it’s been a while, and as a result I didn’t fully remember the way. Three times I got lost, turned around, and had to backtrack. None of them were terrible mistakes, but they reminded me how easy it is to lose your way if you don’t pay attention to your surroundings or have a good map to reference. Having the GPS tracks from those hikers saved me so much time—and likely a lot of extra miles of wandering.
For the Mountains
If you are exploring New Hampshire’s mountains and looking for other great hikes, you can find more at In the Mountains or at NH Peaks. Enjoy it out there!
Update: If not Wrong-Way Matt, maybe Yurg would be a better name for the site. Because that’s the sound I make these days when I get up in the morning.