A few miles north of Woodstock in Shandaken Wild Forest, is Rochester Hollow. A long dirt road which feels akin to trespassing reveals the start of the 5.6-mile loop through the woods.

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Andrew forging a small river, Duluth Pack in tow.
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Raise the roof.

The hike begins with an uphill climb along a creek, and the ascent is slow and steady until reaching the furthest point of the trail, at which point there’s a turnaround to head back.

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Stone walls from early settlers remain, intricately built to last forever like those which roam the Irish and Scottish countrysides.

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At the top of the trail is a lean-to for camping, an impeccably kept shelter in the style of a log cabin, and a bench with a view.

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Chipmunks and birds scatter about while the bears sleep.

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After our multi-hour expedition, we recover and reboot at the Peekamoose. It’s a gorgeous bar and restaurant just around the bend from the trailhead. The bar is adorned with forest-like wallpaper and taxidermy animal heads. Outside a fire-pit is lit and visitors can enjoy s’mores nightly. Bar patrons are jovial with each other, the local Monday night crowd.

Our meal was scrumptious and began with delicious brews on tap and homemade breadsticks. We enjoyed a three-course meal for Restaurant Week seated right at the bar: beet soup to start; followed by cod; and concluded with homemade blackberry ice cream. It was a beautiful, welcoming setting and the perfect meal to follow a hike at Rochester Hollow.