Sherman's Lookout via Prediger Road Trail Head(edit)

Mid September must be one of the best times to summit Indian Head. For the best experience, I’d encourage a clockwise way of summiting and then looping back. We headed out mid morning, signed in at the trailhead and moved through the forest. Slowly making it higher and higher. There are a LOT of roots and you’ll need to keep your feet high so as not to catch your boots and suffer an reverse ego trip. The ground was damp and to some extent wet , but never over the toes of my boots. All of this time we wore baselayers and a vest - it was low 50°’sF: 10°C At the junction the trails switches from red to blue markers this is where the work begins. Roots turn to rocks but the forest is spectacular and you’ll be covered from any showers, should they happen and the effort is made all the more charming with the vistas. Be prepared to sweat a little on the ascent. You’ll know you’re on the right route when you come across the blue baseball hat from Maine! At the upper parts of this section you’ll need to make three climbs, almost vertical and you can thank heavens for Mother Nature and her profuse roots that you can hang onto as you make your way up. The first lookout is simply spectacular and the following ones build on it. As with many peaks in the Catskills, the summit is not much to write home about and we simply walked past and started the descent. While the ascent was roots and damp ground with a couple of near verticals, the descent is knee jarring, energy sapping and became frankly annoying. It just makes sense to have a nice time on your way up and thank you Sean @mountain-hiking.com for the recommendation to go clockwise. Our loop took 4+hrs and we’ll sleep well tonight. Have fun. Be safe and healthy and please. Wear a mask when you meet others on the trail.