This page contains affiliate links. Read our complete disclosure here.
If you are planning a trip out to Vermont we highly recommend hiking the Long Trail. The 272-mile trail runs the length of Vermont and can be completed in roughly 3-4 weeks. This is the oldest long-distance trail in the country built between 1910 and 1930. We spent 2 nights, 3 days backpacking on the Long Trail as part of our road trip last summer.
The difficulty of this trail is more than we were used to. A total of 16 steep, wet, and slippery miles hiked, it was the most challenging backpacking trip we traversed. We endured mental challenges, hiked through the elements, saw incredible views, shared stories with backpackers along the way, and gratefully received some “trail magic” from our new hiking friend, Dawn!
We started the hike out at Stowe Mountain Resort. Overnight parking is allowed in a designated parking lot and many day hikers park here as well. For ease of access to the trail the next morning, we slept in the parking lot overnight. We did try sleeping in a pull-off on Vermont Hwy 108 in Smugglers Notch but a park ranger drove by around midnight and said camping wasn’t allowed. He suggested we try to ski resort parking lot. Organizing our packs in the parking lot took some time and we were able to get on the trail by 10:30 AM on Tuesday morning.
The trail immediately began with a steep elevation gain of about 1,600 ft towards Spruce Peak. Heart rate up, sweat dripping, and muscles working, our bodies were slowly acclimating to mountain terrain. The mileage on a mountain goes much slower than the mileage on hills in the Midwest. We had a 4-mile hike to our first shelter at Sterling Pond.
Sterling Pond had many day hikers taking in the view and enjoying a dip in the water. While enjoying the view of the pond we met a fellow backpacker, Dawn. She was planning on staying at the Sterling Pond shelter that night too, so we enjoyed the evening with her. There were also a few thru-hikers at the shelter. There are certain shelters on the Long Trail that have shelter caretakers and these shelters have a $5 use fee. The shelters offer propane, a cooking stove, and are very clean. However, after reading the note left from the shelter caretaker that a 300-pound black bear had been sighted at the pond nearby the day before, we thought cooking dinner at the ski chalet near the shelter was a bit safer. We also decided to sleep near the ski chalet instead of shelter so Daisy could keep her distance from the other hikers at the shelter with 2 dogs.
Our trail friend Dawn, who is local to Vermont, had mentioned that if we met her at the Bear Hollow shelter the next night and hiked out with her, she would give us a ride back to our car at the ski resort. Her car was parked 4 miles down the trail from Bear Hollow on Route 15. This offer was tempting because it meant we didn’t have to hike “out and back” and allowed us to see more of the Long Trail. It also meant we had to hike double what we had planned to do that day! It was also tempting because we had never experienced a “trail angel” quite like Dawn. When I mention trail angel and trail magic, I am talking about the kindness from others out on the trail. Hikers helping hikers, people helping people, it is a community amongst the hiking community. The people you meet on the trail really can make the experience more meaningful.
Needless to say, we took her up on the offer. Fueled by Mountain House granola, we began our hike up Mount Madonna in the wet and foggy elements. Not even a half-mile into the hike the trail got more intense than expected. The photos below do not do justice for how steep the climb really was! There were a few times throughout the hike that I wanted to give up. Every time I sat to butt slide down on a rock, I thought to myself “continuing to sit instead of hiking sounds appealing.” When I did slip on a rock, I held back tears of frustration. It’s moments like this on the trail that create meaningful lessons. Hiking the challenging and steep peaks were reminders that we need to go through ups and downs in life to meet a goal. We cannot sit idle in life, for if we did that, there would be no growth. Moving forward is the only option.
The hike continued. We were relieved when we got to Whiteface Shelter in 4 miles which marked the halfway point of our hike. Andy went to filter water and Sarah just sat. Sitting felt so well deserved. At this point, I was feeling famished and questioning whether we should meet Dawn at Bear Hollow or just make camp right here. When we picked up the trail book and saw a note from Dawn, our trail angel, it was encouraging and pushed us to keep moving forward!
Soaking wet boots and socks, feet already pruned, we continued the hike to Bear Hollow. All we had to do was climb a little and it was “easy” from there. It truly did get easier. The trail began to open up and flatten out, creating more of a Minnesota hike feel. It was a huge relief to hike on flat ground after 5 hours of constant elevation changes on slippery rocks. About an hour of hiking on the flat ground, we saw Bear Hollow shelter. I started screaming with excitement so loud that Dawn could hear us from above. When we reached the shelter Dawn was already curled up in her sleeping bag and had all her wet hiking gear up to dry. We began to do the same, hoping no other hikes would come in later on since we took over most of the shelter with all of our wet gear. It was an early night and the first time we slept in a shelter with no tent covering around us. Sarah has always been hesitant to do this from fears of a critter crawling on her face but after a long day of hiking, anything goes! It was a quiet night and no critters came by. The following morning came with slow sips of coffee and packing up for the easy 4-mile hike out.
Back at the parking lot we said goodbye to Dawn and thanked her for the trail magic, then went our separate ways. After packing our car up and changing into clean clothes, Andy realized we were missing hiking poles! They had been left in Dawn’s truck. We hadn’t exchanged contact information, we had only given Dawn our business card so we were trying to figure out how to get in contact with her. We spent some time in Stowe hoping she would contact us by the time she got home. Our hope was answered and she contacted us while we were enjoying beer and burritos at a local Stowe joint!
To continue the trail magic Dawn invited us to come to get the poles at her house, spend the evening on her property, have a shower, cook us dinner, and enjoy the evening by the bonfire. For more details of our experience with Dawn, take a listen to our podcast episode with her on Hiking Thru Life podcast episode #7 Trail Angel Dawn. It was pure kindness and an example of strangers coming together to form a friendship. We are so grateful for the time spent with Dawn and her willingness to open her home and cooking to us!
What experiences have you had with trail magic or strangers turning into friends? If you can’t think of one, here’s your encouragement to go out and make a friend next time you’re on the trail or wherever life’s journey leads you!
Peace, love, and hike thru life!