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on summit of winn mountain

Needed a Winn

Posted on June 20, 2026June 20, 2026

Nothing was going right. With all of the hullabaloo going on these last few weeks, yesterday I discovered that I had overlooked some critical work orders I needed to address. Then one of the contractors I had scheduled couldn’t complete their work because of an electrical component that was in the wrong place. Then a whole host of to-dos emerged when my work email server, which had been down for the last five days, finally opened back up and revealed everything I had missed. It was just one thing after the other.

I needed a hike.

Late in the afternoon, after ripping through everything I needed to, I announced to my wife that I was heading out to climb a mountain. “Where?” she asked.

“I don’t know,” I said. “But I gotta go.”

“Ok, well, just let me know when you figure it out.”

My stress level was such, I wanted something big. Like Killington, which is about two hours and fifteen minutes from my house. I figured I could be there by early evening, torch that sucker, and then climb down in the dark. It was a dumb idea, but stress can do that to a person.

Fortunately, I never made it to Killington.

About twenty minutes down the road, the skies started to darken, and the idea of getting caught in a lightning storm on Killington didn’t sound very appealing. I decided to pull over. Opening my trusty Peakbagger app, where you can locate nearby peaks, I searched for alternatives. I was approaching Lyndeborough, NH, and Peakbagger indicated that Winn Mountain was pretty close to where I was. Winn. Winn. Hmmm.

Winn and I have a history. I tried climbing it twenty years ago or so, back when it was a freshly cut forest and there was no sense of a trail. It looked like a logging area—the kind where the earth is devoid of plant life and the surrounding trees make the area look gloomy, even on a sunny day. It felt like hillbillies could emerge out of the underbrush at any moment and take me on a ride from which I would never return.

I tried it once more a few years later, armed with a ViewRanger app on my phone, but failed to find the summit then as well. The only thing I was able to find, again, was a good case of the willies. So, you’ll forgive me if I wasn’t jumping at the chance to see Winn again. But with an unreasonable drive to Killington and cloud cover forming, it seemed to be a better alternative. Plus, I had recently read online that a marked trail was available now and I had seen some GPS tracks on Peakbagger from other climbers. This time, I knew, there would be a way to successfully find the summit—even if it scared the crap out of me.

And I was right!

New landowners recently reopened the old Schwartz Trail leading to the summit, delineating it with new trail signs and a clear path. It’s a welcome change and a generous gesture on their part. You can tell it’s still relatively new because some spots have plenty of grass, including one patch that you know is teeming with ticks because of all the tallgrass. (It was, and I found a jumper on my shirt.) But for the most part, the Schwartz Trail runs smoothly at a nice easy elevation grade. And it’s totally worth it for the view.

I’ve climbed neighboring Rose Mountain several times and always found the view from its top somewhat disappointing, but this was not the case on Winn. On Winn there is a striking view of North Pack Monadnock, Monadnock Mountain, and Pack Monadnock. It’s absolutely beautiful and I lingered for a bit to take pictures and soak up the scenery. If I had brought some food, I probably would have taken a nice little snack break. I couldn’t believe my luck. After thinking for so long that Winn was a good-for-nothing, ugly little mountain that couldn’t possibly offer any views because of its lower elevation, I found one of the best views I’ve ever seen in this part of southern New Hampshire. I just needed to be willing to give it another look.

Makes me wonder what else I need to do that with.

  • view from winn mountain
    A Fantastic View!
  • winn mountain trailhead
    Clear Trailhead Sign at end of Joslin Rd
  • top of winn mountain
    Approach to the summit of Winn Mountain
  • winn mountain summit
    Cairn at the summit
  • sign to winn mountain
    More Signage towards the top
  • sheep laurel
    Sheep laurel
  • spooky tree schwartz trail
    Still spooky things to see on the trail
  • peak visor view winn mountain
    PeakVisor’s mapping of the surrounding peaks

Winn Mountain Ascent Details

Trail: Schwartz Trail (via Joslin Road)
Distance: 2.8 miles round trip
Elevation Gain: ~700–775 ft
Summit Elevation: 1,680 ft
Difficulty: Easy to moderate, gentle grade throughout
Location: Lyndeborough, NH

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