Hiking Trails & Parks in Winchester, Maryland
30 trails & 0 parks in Winchester, located in Winchester County, Maryland.
About Outdoor Recreation in Winchester, Maryland
Winchester offers 30 mapped hiking trails and 0 federally managed parks within the city or nearby. Located in Winchester County, Maryland, it’s a starting point for hikers, campers, and casual nature seekers.
Explore more nearby: Winchester County overview, all Winchester County trails, or statewide Maryland list.
Hiking Trails in Winchester
From the OutsideAtlas Blog
Photo: Tobias MrzykThe 10 Longest Hiking Trails in Maryland, Ranked
Maryland's longest mapped hiking trails, ranked by distance with notes on what makes each route worth the commitment.
Photo: Tobias MrzykMaryland's 10 Most Punishing Trails by Elevation Gain
Steep is hard. These are the ten Maryland trails with the most total elevation gain — quad-burners earned by hard climbing.
Photo: Maddi BazzoccoThe Best Beginner-Friendly Hikes in Maryland
Ten gentle, well-marked Maryland trails perfect for first-time hikers, families, or recovery days.
Photo: Tobias MrzykThe 10 Most Challenging Hikes in Maryland
Maryland's ten hardest hikes — expert difficulty, big mileage, or serious exposure. Reserved for experienced hikers.
Photo: Diego LozanoThe Best National Parks & Recreation Areas in Maryland
Federal parks and recreation areas in Maryland ranked by what they actually offer hikers and campers, not just popularity.
Photo: Tobias MrzykBest Waterfall Hikes in Maryland: 10 Trails to See Falls Up Close
Maryland's best hikes to named waterfalls — from short family-friendly viewpoints to all-day cascade chasing.