Cheshire County, New York
408 hiking trails · 0parks & campgrounds · 26 cities. Real OpenStreetMap + Recreation.gov data.
About Hiking in Cheshire County, New York
Cheshire County is home to 408 mapped hiking trails and 0 federal parks, campgrounds, and recreation areas spread across 26 cities. Trail data is sourced from OpenStreetMap contributors; park and campground info comes from Recreation.gov.
Looking for something specific? Search all trails in Cheshire County or browse parks. Want to narrow further? Pick a city below to see only that city’s outdoor options.
Trails & Parks in Cheshire County
Up to 200 pinpoints showing trail and park locations across the county.
Cities in Cheshire County
Click any city to see trails and parks within it.
2 more cities in this county.
Sample Trails in Cheshire County
Hiking guides for New York
Statewide rankings and guides — useful context for Cheshire County.
Photo: Sergei AkulichThe 10 Longest Hiking Trails in New York, Ranked
New York's longest mapped hiking trails, ranked by distance with notes on what makes each route worth the commitment.
Photo: Joshua EarleNew York's 10 Most Punishing Trails by Elevation Gain
Steep is hard. These are the ten New York trails with the most total elevation gain — quad-burners earned by hard climbing.
Photo: Maddi BazzoccoThe Best Beginner-Friendly Hikes in New York
Ten gentle, well-marked New York trails perfect for first-time hikers, families, or recovery days.
Photo: Holly MandarichThe 10 Most Challenging Hikes in New York
New York's ten hardest hikes — expert difficulty, big mileage, or serious exposure. Reserved for experienced hikers.
Photo: Diego LozanoThe Best National Parks & Recreation Areas in New York
Federal parks and recreation areas in New York ranked by what they actually offer hikers and campers, not just popularity.
Photo: Tobias MrzykBest Waterfall Hikes in New York: 10 Trails to See Falls Up Close
New York's best hikes to named waterfalls — from short family-friendly viewpoints to all-day cascade chasing.