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  • Writer's pictureIzzy Risitano

The Best Way to do Wilson and Breadloaf | 10/8/22 - 10/9/22

Updated: Mar 2

I had committed to leading a handful of Mountain Leader Course trips for my college this fall and some of those happened to be overnights, as per my request. As soon as I found out who my co-leader was, I sent him a text with my idea, followed by “Probably some sort of car spot between skylight pond and Emily proctor or Emily proctor and Cooley Glen.” Grammatical errors are included for accuracy. At the time, no other decisions were made, it was still August for crying out loud but I needed to figure out which peaks I was bagging for my hundred so I could keep myself accountable. Greg said he liked my idea, and that was that. We didn’t talk about it for another 5 weeks.

Sunset from Sunset Rock

With the first half of the semester flying by faster than I could’ve imagined, I started getting emails from our directors about locking down a destination and began a storm of trip-planning ideas. From my Long Trail map to Caltopo, to aggressive zoom-ins and outs on Gaia, I wanted to make sure this trip would do more than bag peaks and be something everyone enjoys. With this in mind, I negotiated for a car spot that started at Emily Proctor and Ended at Skylight Pond. I was estimating 8.27 miles and about 2,500 gain for the feat, which is reasonable for a beginner backpacking trip.

As the days counted down to our trip, the numbers got sparser. We started with 4 people and 2 instructors and by the time the packing meeting rolled around we were left with one. We had an out on the trip, it was silly to arrange a full car spot and gear set-up for one participant, but Greg and I felt confident it would be worth our while as AJ came to every trip with an unmatched level of enthusiasm. We could not have been more right in our judgment.

A pleasant drive to central Vermont

The morning of the trip, the guys hopped in the van while I drove my car down to the Green Mountain National Forest so that we could arrange the car spot. I was amazed by the beauty and resemblance Route 125 held to my home state’s Kancamagus Highway, minus the crowds of course. In just over an hour, we dropped my car at Skylight Pond and proceeded for Emily Proctor in the van. When we got to the turn for the trailhead, we were disheartened to see a “rough road” sign, as the vans struggle on perfectly normal roads. With this, we opted to park on the dirt road and walk up to the trailhead.

Very eclectic property on the way to Emily Proctor/Cooley Glen TH

The walk was only about a third of a mile, and upon inspection, I believe that we could have gotten the van up it despite the hefty warning. Either way, we excitedly started up the trail, after passing a unique private property stretch, and the colors were incredible.

Entering the Breadloaf!

Emily Proctor begins with a bit of elevation before turning into a very gradual gain for about two miles. For the most part, we meandered through an attractive maple forest with occasional stream crossings for a while before getting to our last 0.7-mile push to the shelter. In this stretch, we encountered nothing technical but were certainly worked by the elevation gain while battling being so cold and so hot at the same time… and no wonder, there was snow!

Relics along the way

Fall to Winter real quick

Before we knew it, we got up to the lean-to and even though we had planned to stay there that night, we looked at our watches and felt it would be ridiculous to set up camp at noon. So, we walked on to Wilson which started with some light heart-pumping effort and evened out to a flat walk to the true summit and then a small decline to the viewpoint. Despite only getting the tiniest window for a lookout, the contrast between the frost where we were to the sea of colors down below was magnificent.

Emily Proctor lean-to

Wilson lookout

After Wilson, we double-backed to the Long Trail and kept on to Breadloaf. The second peak was acquired with a small and doable spur off of the Trail. The summit was entirely viewless and marked with a small and very unsymmetrical cairn. Boom, I had hit #62 and so far was loving what most would consider the most underwhelming peaks.

Breadloaf summit!

After Breadloaf, we got to Skylight Pond before I knew it and even the “worst” elevation losses on the trail were very manageable and well-kept by the lovely GMC. We went down to camp, got set up, and then needed to pump water. We don’t use the best pumps on school trips, but they’ve always worked. Skylight Pond, however, was nasty. It took 10 seconds to filter one pump of water out with a considerable human effort to do so. Though there was a sign pointing to spring higher up on the shelter sput trail, this was the “spring” in question. Believe it or not, this still filtered slightly better than the pond.

Skylight Pond

Our lone participant, AJ, pumping out of the sad spring

After finishing our camp chores, we hiked so much faster than I had estimated that it was only 4 pm. We sat around in every layer that we’d brought and played the 5-second rule game while we awaited the sunset. At that point, we headed back up the spur trail to the Long Trail where we took a left in search of Sunset Rock. When we quickly found an unmarked but well-traveled spur, we took it and were surprised to find such a nice view. Still unsure if this was THE Sunset Rock, we walked a tad further down the trail but did not find anything else. So, we returned to the majestic spot and awaited an incredible sunset over Lake Champlain and the peaked foliage.

AJ & Greg on Sunset Rock

After sunset, we returned to camp where we were greeted with an even more incredible sight, a MOONRISE. I rarely ever see these, and getting the opportunity over Skylight Pond made it even more special. The moon changed from pink to white so quickly and my attention could not be diverted from it until it was time to start cooking after the sky had darkened.



For dinner, we made Santa Fe-style rice and cleaned up with hot drinks before shutting in. Due to the cold and a real feel of 12 degrees, we knew it was in our best interests to zip up and get into our zero bags as soon as possible. The first 2-3 hours of my attempted sleep were unsuccessful as I alternated boiling and freezing. Eventually, I fell into a broken sleep until about 7:30 in the morning, for which I woke up very warm.

In the morning, unable to pump more water all that well, we opted for a dry breakfast and got going early down Skylight Pond Trail and completed its 2.5 miles in exactly an hour. Along the way, we heard a pack of coyotes, which was terrifying to hear at 9 am, and ran into another party shortly thereafter. In the trio, one of the members seemed to have acquired every patch from every list. If you’re reading this, your pack and your accomplishments are so awesome, it’s rare to see them all sewn on that well, haha.

Heading down Skylight Pond Trail

Once we got to the trailhead, I fueled up on electrolytes, drove to the van to complete the car spot, and headed out North toward Lincoln. All said and done, I am beyond happy that we opted to stay at Skylight instead of Emily Proctor. The shelter was astronomically nicer, we had views of the east and west, and it allowed us to have a very quick way out in the morning, which was appreciated as we woke up to light flurries.

Bye Breadloaf Wilderness!

If you still need to bag Wilson and Breadloaf, the time is now. These mountains are far more beautiful than they get credit for and Vermont could not be more stunning right now.

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