Hiking Trails & Parks in Winchester, Vermont
13 trails & 0 parks in Winchester, located in Cheshire County, Vermont.
About Outdoor Recreation in Winchester, Vermont
Winchester offers 13 mapped hiking trails and 0 federally managed parks within the city or nearby. Located in Cheshire County, Vermont, it’s a starting point for hikers, campers, and casual nature seekers.
Explore more nearby: Cheshire County overview, all Cheshire County trails, or statewide Vermont list.
Hiking Trails in Winchester
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.