Monadnock-Sunapee Greenway Trail: Day One (NOBO, Late April 2026)

Establishing

It was a foggy morning in Western Mass and I woke up very nervous to start my hike. I had never backpacked alone and suddenly felt like a lot could go wrong; Many “what ifs” ran through my mind. What happens if I’m cold and can’t sleep? What if I forget something essential, like my headlamp? What if I feel incredibly lonely without Sam and Wiley? I checked my equipment and made sure I didn’t forget anything, and decided to change my 30 degree quilt to the 10 degree quilt. There was nothing I could do about the loneliness except go out and see what happened.

After breakfast, I said goodbye and began the two-hour drive to Monadnock State Park. As I entered Vermont, the fog lifted and my anxiety seemed to do the same. It was turning out to be a beautiful spring day with blue skies and highs around 60 degrees that we looked forward to.

I put Paul Simon’s. Rhythm of the saints into the CD player and let the music take me back to a time before the worries of adulthood played any role in my life. Freedom was such a palpable feeling back then; It seemed to always be within reach.

I saw a blue heron fishing in a small roadside stream as I continued cruising through southern Vermont. It seemed like a good omen. Before I knew it, I was arriving at the Monadnock State Park headquarters. I gave my name to the people at the booth and they gave me a tag for my car, which meant I would walk around MSG and come back in four days for my car. I parked, scarfed down some overnight oats, and put on my backpack. I locked up, put my keys away, and headed to the start of the White Dot Trail. I would take you to the junction with the White Cross Trail, a slightly less steep trail that you would take until reconnecting with the White Dot Trail just before the summit.

Mount Monadnock

Before setting foot on the trail, I weighed my backpack at the Visitor Center: 30 pounds. Not bad with four days of food and enough water to get to the other side of Monadnock! I was worried that my backpack would be much heavier, but I could live with 30 pounds. As soon as I put my backpack back on, I heard someone say, “Are you going to walk the Greenway?” Thus began my conversation with Paul, a local in his 70s who was no stranger to Monadnock and who seemed to have a penchant for all things hiking. I walked with him to the crossroads; He set a nice easy pace and I was happy to take my time and chat as I began the most challenging climb of my walk. As we talked, what was left of my worries faded away.

At the junction with White Cross Trail I said goodbye and continued on my way. The trail climbed moderately for 1.3 miles up a rock staircase before breaking through the tree line and meeting the White Dot Trail for another 0.3 mile of open slabs with incredible views to the top. I saw a few hikers descending the White Cross Trail and a handful of people at the top, but for such a beautiful morning the trail wasn’t as crowded as I’m sure it would have been on a weekend.

The beginning of the ascent along the White Cross Trail.

First view of the summit.

Getting closer…

The summit was amazing, with 360-degree views of pine trees, ponds, and distant blue mountains, but due to the intense wind and cold, I didn’t stay long. There were many more views during my descent down the Dublin Trail.

One of the many views of the summit.

On the Dublin road

He still maintained that nice, calm rhythm that Paul had set before; Even though I had started late, I basically had all day to walk eight miles. The descent was tricky at times and I felt the weight of my backpack at those times, but other than a slab that I had to slide down, I felt safe at my slow pace. The wind was persistent and despite leaving the views behind, I was ready when the trail rejoined the forest. It’s time to take off my backpack for a few minutes, relax and have a snack.

back in the forest

76.4 km to Sunapee

The descent gradually smoothed out, passing through a burnt area and then turning onto a country road; A short walk along the road was very welcome after having completed the most strenuous part of the entire Greenway. The remaining three miles of trail were an easy hike through the woods without much elevation change. I stopped for lunch at a small spring and refilled my water bottles before continuing towards Spiltoir Shelter, where I would spend my first night alone in the forest.

making camp

When I arrived at the shelter, I signed up for the trail registry. The last NOBO hiker had checked in six days ago, so I doubted I’d find anyone heading in my direction, but a SOBO group had checked in the night before. I had hoped to meet at least some fellow hikers on the Greenway, but I hadn’t seen someone following the trail since I left Monadnock State Park.

Spiltoir Refuge

Install

I hung my hammock, had dinner, and spent a frustrating hour searching for a suitable tree and hanging my bear bag before bed. I planned to hike 19.4 miles to the Fox Brook campsite the next day, so I wanted to get an early start. When I got into my hammock, I was glad I brought the 10-degree quilt. It looked like it was going to be a cold night.

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