Weekend On Windmill Ridge
Stunning views, a cabin at the top and more than 25 miles of trails make this parcel of preserved land worth a trip from anywhere in Vermont.
Story and photos by Bill KimballAbout two years ago, not long after my girlfriend Jen started working for the Vermont Land Trust, 
she texted me a photo of a sweet-looking section of trail along a forested ridgeline in Westminster, in the southern part of Vermont.
You could see the track winding gently up a slope beneath a peaceful green woodland. She said it was all really nice like that, and we agreed that we’d need to make a trail running trip there sometime.
On July 4th of 2017, we decided to try it out on a 10-mile trail run. After grabbing some sandwiches-to-go at the Putney Co-op, we navigated up the pretty back roads of Putney and Westminster to the base of a long north-south mountain called Windmill Ridge. We parked at the trailhead for the Holden Trail and got ourselves ready. We acquired GPS signals, re-checked hydration packs, put on sunscreen, and determined that bug spray, thankfully and amazingly, seemed unnecessary. With all systems go, we set out up the trail from the gate.
We got incredibly lucky with conditions: the temperatures were just right, puffy clouds drifted in the sky, and we only saw a few mosquitoes. Crowds were light too, especially considering it was a holiday. There was only one other car in the lot on when we arrived, and a handful of people were picnicking up on top of The Pinnacle; otherwise, the only other person we saw all day was a trail maintenance worker on the ridge just north of Holden Knob.
The initial ascent was fairly easy. We ran along a wide path, and then along a recently relocated singletrack section that was clearly laid out by people who love trails as much as we do. The winding path felt like it belonged there. Following the natural flow of the landscape, it dipped and climbed around a series of ledges and swales, but it always remained runnable. In just over a mile, we reached the Pinnacle Trail along the crest of the ridge.
Heading north from the trail junction, we jogged the mile or so up to the summit of The Pinnacle. Along the way the trail gently rose and fell, making for very pleasant running. It was about 80 degrees outside, but the humidity was low, and a light breeze kept us from overheating. At the top, there is a cabin (which you can reserve for overnights) with fantastic views.
The Pinnacle is the highest and most scenic peak (1,683 feet) in Westminster, Vermont. You can see clear to Hedgehog Gulf in Brookline and westward to Mount Snow and Stratton Mountain, more than 20 miles away. A few scattered clouds hung on the horizon and occasionally passed overhead. And it was blissfully bug-free for a warm July day.
From the Pinnacle, we continued running north for about 2.5 miles to the network of trails below Paul’s Ledges. We managed to hit most of them, including the surprisingly challenging Hemlock Trail. Staying on the right path required a little bit of attention to the map, but fortunately we’re both map geeks and love the game of route-finding in new places, so we didn’t get lost.
I had something else on my mind at that point—something important—and was secretly just looking for a setting other than the next bend in the trail. At last we climbed to the clearing at Paul’s Ledges, where we found ourselves alone on a ridge above the idyllic Vermont countryside on a gorgeous afternoon. I waited for a quiet moment, then turned to Jen and looked her directly in the eye and proposed to her on the spot.
She said yes.
After sharing a celebratory Snickers bar (hey, if it works at the time, go with what you’ve got), we headed back south along the ridge with renewed energy and enthusiasm. Our feet felt light and airy, dancing over the occasional rocks and roots. This time, just before reaching the top of The Pinnacle, we turned left and headed down the Holden Trail. It’s clearly one of the older (and more eroded) trails on the mountain, but parts of it are still really fun to run, and we literally whooped and giggled the whole way down.
Overall, it was a great introduction to running the trails of the ridge, not to mention a memorable landmark in our relationship. We both felt invigorated after the rugged ten-mile trek, and we couldn’t wait to go back and link up with other parts of the interconnected network, including trails on Putney Mountain to the south and in the 207- acre Athens Dome area to the north. It’s definitely a first-rate destination for anyone looking to get out for an adventure in southeastern Vermont.
Ben Kimball is the author of Trail Running Western Massachusetts, available on Amazon.com