Explore Cheshire County Hikes by Distance, Elevation, Difficulty, and More

Check out some of the best hiking, walking and backpacking routes in Cheshire County, New Hampshire. The Monadnock-Sunapee Greenway is the most popular trail. The trails have 7 user reviews with great photos and information. There are trails of various difficulty levels including easy and medium. The trail with the highest elevation climb is the Monadnock-Sunapee Greenway and the trail with the least amount of climbing is the Hubbard Farm to Connecticut River Trail. The longest trail is the New England Trail at 349.1 km. For a shorter adventure you can try the White Brook Road Loop at 648 m. Get off line access to Fastfood, Restaurant, Town, and Peak locations and much more with a Hiiker subscription.