9.0 miles | 2,198 ft gain | Difficulty: Moderate | Rating ★★★★

Heading up to the Catskills for the long weekend, we had worried we made a mistake. We first debated going up to the Adirondacks, but we have another road trip coming up and wasn’t up for two 5+ hour drives so close to each other. So we settled for the Catskills. The weather promised clouds, lots of them, and the photos I’ve seen this past week were still quite green. Luckily, the foliage sped up just for our arrival.

After Plateau kicked our butts earlier this summer, and with the lack of high elevation gains under our belts this year, tackling another (or two) Catskills 35er felt intimidating. Especially along Devil’s Path. We opted to go out and back via the Jimmy Dolan Notch trail, bringing us to 3100 feet, in between the two mountains, allowing us to choose one, the other, or both.

The Jimmy Dolan trail boasted about 1000 feet of elevation gain, but from its gradual increase through a wide forest, you would never know. There were roots and rocks to navigate, but that’s to be expected. It was only after we turned around a bend with about .3 miles left to the Notch that we hit a steep bit, bringing us up some small rock scrambles fast.

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Once at the Notch, we decided to go right to Twin, the longer of the trails with more promising views. We met several scrambles, but still nothing too challenging. At the mountain’s southern peak, we got wide views of the rest of Devil’s Pass, as the clouds parted at the right moment. A half mile further to the northern and true summit, we were met with thick pines and limited views.

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After stopping for lunch, we made our way back down to the Notch and hesitated for a bit as to climb Indian Head or give up for the day. After some encouragement from another hiker, we continued on to the half mile 459 foot climb. The true summit is just a wooded part of the trail. A bit further past there were supposed views, but with the clouds rolling in, we decided to just make our way home.

Unlike its sibling, Plateau, Indian Head and Twin were much milder. They were the perfect climbs to remind us, we are worthy of these mountains, and give us the confidence boost to explore more.