These challenges listed below are not for the faint of heart. The Catskill Mountains are challenging peaks with steep ascents and descents, challenging terrain, lack of water in certain seasons and varying weather conditions all year long. Hike On Guides have successfully completed all of these challenges and would love to help you complete yours. For folks new to the Catskills Hike On Guides suggests starting with the 3500 peak challenge. The remaining challenges are only recommended for those in top shape, though by finishing your 3500 peak challenge you are ready to take on a new challenge.

Contact us to set up a challenge date or for more information.

  • The 3500 Peak Challenge: The Catskill Park is home to 35 mountains that are 3500 feet or higher in elevation. This challenge is to climb all 35 of those peaks, as well as 4 in the winter (for a total of 39 climbs). One can also do this as a winter challenge, climbing all 35 peaks between December 21 and March 21. On completion one becomes a 3500er. More information can be found on the Catskills 3500 Club webpage.

  • Devil in a Day: This challenge is to hike the entire Devil’s Path in one day (under 24 hours). The Devil’s Path is 24.2 miles long and traverses over the mountains of Indian Head, Twin, Sugarloaf, Plateau, the shoulder of Hunter, West Kill and St Anne’s Peak. It can be traversed in either direction. The steep ascents and descents of over 2000 feet on repeat make this one of the most challenging trails in the east.

  • All Trails Challenge: The Catskill Park has nearly 350 miles of marked trails within in the Park. To successfully complete the All Trails Challenge one must hike all 350 miles of marked trail within the Catskill Park. More information can be found on the Catskill Mountain Club’s webpage.

  • Hike the Burroughs Range in a day: This 9.8 mile trail runs from Woodland Valley Campground to the Slide Mountain Wilderness parking area. The trail traverses the peaks of Wittenberg, Cornell and Slide Mountains. Though not as long as the Devil’s Path and the Escarpment Trail, the Burroughs Range with its steep ascents and descents and a few technical spots is still quite the challenge.

  • Hike The Escarpment Trail in a day: This 23.9 mile trail runs from route 23 in Windham to Schutt Road the town of Hunter. Much of the trail is along the cliff lines and ridges on the Eastern Escarpment of the Catskills. The trail runs over Windham High Peak, Burnt Knob, Acra Point, Blackhead Mountain, Arizona Mountain, Stoppel Point, North Point and thru North/South Lake Campground. Similar to the Devil’s Path the steep ascents and descents on repeat can make this a challenging day hike. Throw in the lack of water along the route, which only adds to the challenge.

  • Manitou’s Revenge: This 56 mile traverse of the Catskills is not for the faint of heart. There are crazier people who run it in a 24 hour timeframe. This challenge is to hike not run the 56 mile traverse in 48 hours. Starting in Windham and ending at the Mt. Tremper parking area on Old Route 28. This traverse brings you to all the best the Catskills have to offer.