All Hiking Trails in Cheshire County, Vermont
406 trails across Cheshire County. Search by trail name or city.
Page 1 of 9 (406 total)
From the OutsideAtlas Blog
Photo: Tobias MrzykThe 10 Longest Hiking Trails in Vermont, Ranked
Vermont's longest mapped hiking trails, ranked by distance with notes on what makes each route worth the commitment.
Photo: Sergei AkulichVermont's 10 Most Punishing Trails by Elevation Gain
Steep is hard. These are the ten Vermont trails with the most total elevation gain — quad-burners earned by hard climbing.
Photo: Tobias MrzykThe Best Beginner-Friendly Hikes in Vermont
Ten gentle, well-marked Vermont trails perfect for first-time hikers, families, or recovery days.
Photo: Joshua EarleThe 10 Most Challenging Hikes in Vermont
Vermont's ten hardest hikes — expert difficulty, big mileage, or serious exposure. Reserved for experienced hikers.
Photo: Joshua EarleThe Best National Parks & Recreation Areas in Vermont
Federal parks and recreation areas in Vermont ranked by what they actually offer hikers and campers, not just popularity.
Photo: Sergei AkulichBest Waterfall Hikes in Vermont: 10 Trails to See Falls Up Close
Vermont's best hikes to named waterfalls — from short family-friendly viewpoints to all-day cascade chasing.