Jackson Mountain 10/21/2026

On this perfect late October day, we headed to Tumbledown Public Land for a loop hike over Jackson Mountain. Although it stands taller than its more popular neighbors, Jackson Mountain sees far less traffic, and, in my opinion, is one of the more underrated mountains in the area. We started at the Morgan Road Trailhead, and hiked downhill on the Little Jackson Connector Trail. After reaching the Brook Trailhead, we headed west on the Byron/Weld Road. After a road walk of a few miles, we turned onto the logging road following the Stockbridge Branch of the Swift River. Shortly before the bridge over the river, we turned onto the trail which follows the Stockbridge Branch along the north side of the mountains.

Road walk on the Byron/Weld Road

This seldom used trail provides a longer, but more gradual approach than the busy trails on the south side of the mountains. It follows the stream valley up, following the route of an old tote road for a while, before diverging on its own path as it turns away from the main stream and heads south up the mountainside. Upon reaching Jackson Pond, we took a break at the cabin and enjoyed the beautiful high elevation pond before continuing.

Cabin on Jackson Pond

Inside the cabin

Jackson Pond

After leaving the pond, we turned onto the Jackson Mountain Trail for the final ascent to the top. The Jackson Mountain Trail has got to have the most beautiful extended mossy sections of any trail around! We stopped to enjoy the beautiful viewpoint, offering a unique close-up view of Little Jackson, before reaching the summit clearing.

Little Jackson Mountain from Jackson Mountain

View northwest

View south

With clear skies and no wind, it was a perfect day to lay in the sun on the helipad for a while, which we did while eating lunch. After lunch, we went back down the Jackson Mountain Trail before following the Little Jackson Trail on a much more direct route to our car. Surprisingly, we didn't see anyone else on the trails all day, even in the area of Little Jackson, and we were the only car in the parking lot both when we started and when we left.

Sampson at the summit of Jackson Mountain

View towards Mount Blue

View back towards Jackson Mountain from the saddle between Jackson and Little Jackson

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Blueberry Mountain 10/12/2026

Opting for a short local hike today, we headed over to Blueberry Mountain in Township 6 North of Weld. At 9:00, we were the first car in the parking lot. As we headed up, we were unsure whether or not we would be in the clouds when we reached the summit. The trail remains in pretty much the same condition that it has been for the last ten years, mostly clear and well marked, but somewhat eroded in steeper sections.

The trailhead

View towards Webb Lake on the way up

Geodetic Survey marker at the summit

We were still in the clear as we approached the summit, and we were treated to sunny skies at the top. It was a bit windy, and many of the surrounding peaks, including the Jacksons were in the clouds, but it remained sunny on top of Blueberry for the 2+ hours that we spent at the summit. Although the foliage was past peak, the colors were still beautiful, and the warm sun made it the perfect day for an extended summit stop. We saw one other group at the summit, and one more while we were descending, but it wasn't too busy at all for a holiday weekend!

View north towards the High Peaks

View west towards the Jacksons

View southeast towards Mount Blue and Webb Lake

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Bald Mountain (Woodstock) 10/8/2026

On this beautiful fall day, we found our way back to Bald Mountain in Woodstock to explore a few trails that we hadn't hiked yet on the mountain. We were the first car in the Little Concord Pond State Park trailhead lot at around 8:30, and we started up the trail to Little Concord Pond. Upon reaching the pond, we opted for the trail heading along the west shore of the pond.

Little Concord Pond State Park Trailhead

At the pond's most northwestern point, we found the first, and most mysterious, of the three new trails that we planned to explore. I had noticed this trail before, but was not able to find any maps showing it or references to where it went. We started down the trail, and it soon became clear that although the trail was lightly used, it was well cared for with no real blowdowns at all and a clear trail corridor. The trail descended a bit as it wound through the forest. Eventually, the trail popped out at the end of a woods road, and we realized that we were at the end of Pelletier Road near Concord Pond. It was great to discover this new approach to the trails on Bald and Speckled Mountains!

Little Concord Pond

After retracing our steps back to Little Concord Pond, we took the trail heading northeast towards the logging roads on the north side of Speckled Mountain. Just before the trail reached the logging road, we took a right turn on a somewhat eroded trail heading uphill. This was the second new to us trail which climbed rather gently to the south. The trail had some blowdowns, but was easy enough to follow, and it became rather level as it reached the wide col between Bald and Speckled. We reached the 4-way junction in the col with the blue-blazed Speckled Mountain Trail. After determining that the trail south of the col was too muddy and overgrown to be worth following, we headed west to the summit of Bald Mountain.

Speckled Mountain from Bald Mountain

Sampson at the summit of Bald Mountain

View west from the summit

Despite the beautiful weather foliage, we had the summit of Bald completely to ourselves for over an hour while we relaxed and ate lunch. Just before we left, we did see one other hiker with her dog, one of only 3 people we would see during the hike. Continuing west from the summit, we soon took a sharp left turn onto our third, and final, new trail of the day. This unmarked, but well used path soon took us to the bottom of Shagg Crag, the popular rock climbing cliff on Bald Mountain. The cliffs were very imposing from the base, and they were covered in climbing hardware. The trail took us through the rubble along the base of the cliff. We passed one pair of climbers along the way. Soon past the end of the cliffs, the trail reached a viewpoint on top of a tall ledge. I had no idea that this southeast facing viewpoint existed, and it was the best kind of surprise when exploring a new trail!

Shagg Crag

Can you spot the climber?

After enjoying the beautiful view towards Abbotts Pond, we headed back along the trail, and down to where our car was parked. It was a very successful day of new trail exploration, and now I have been down every notable trail that I am aware of on Bald and Speckled Mountains.

View southeast from the viewpoint near Shagg Crag

View south

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Wyman & Hall Mountains 10/1/2026

Today, we wanted to choose a good hike for the peak foliage, and we settled on Wyman and Hall Mountains in Andover North Surplus. Having previously hiked both mountains last summer from South Arm Road to the north, this time we opted for the more direct approach from East B Hill Road to the south.

Starting our hike from East B Hill Road

Surplus Pond

We started the hike up the mountain on a relatively easy, but steady, ascent on the Appalachian Trail. We soon entered a beautiful hardwood glade with vibrant yellow foliage, before a short descent to Surplus Pond. Surplus Pond is a picturesque backcountry pond which was ringed with stunning foliage today.

Trail sign near Surplus Pond

Sampson in Surplus Pond

Past the pond, we ascended to the ridge on Wyman Mountain and reached the viewpoint near the summit. As hoped for, the views of the surrounding mountains and valley blanketed in reds and yellows was stunning. We continued on to the viewpoint on Hall Mountain before returning to Wyman Mountain for lunch.

A pretty section of trail on the way up

View from Wyman Mountain

After lunch, we retraced our steps back down to East B Hill Road. It was an excellent foliage hike to avoid the crowds, as we only saw two other groups out on the trail.

Hall Mountain Lean-To

View from Hall Mountain

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