Westchester County, Connecticut
719 hiking trails · 0parks & campgrounds · 20 cities. Real OpenStreetMap + Recreation.gov data.
About Hiking in Westchester County, Connecticut
Westchester County is home to 719 mapped hiking trails and 0 federal parks, campgrounds, and recreation areas spread across 20 cities. Trail data is sourced from OpenStreetMap contributors; park and campground info comes from Recreation.gov.
Looking for something specific? Search all trails in Westchester County or browse parks. Want to narrow further? Pick a city below to see only that city’s outdoor options.
Trails & Parks in Westchester County
Up to 200 pinpoints showing trail and park locations across the county.
Cities in Westchester County
Click any city to see trails and parks within it.
Sample Trails in Westchester County
Hiking guides for Connecticut
Statewide rankings and guides — useful context for Westchester County.
Photo: Joshua EarleThe 10 Longest Hiking Trails in Connecticut, Ranked
Connecticut's longest mapped hiking trails, ranked by distance with notes on what makes each route worth the commitment.
Photo: David MarcuConnecticut's 10 Most Punishing Trails by Elevation Gain
Steep is hard. These are the ten Connecticut trails with the most total elevation gain — quad-burners earned by hard climbing.
Photo: Tobias MrzykThe Best Beginner-Friendly Hikes in Connecticut
Ten gentle, well-marked Connecticut trails perfect for first-time hikers, families, or recovery days.
Photo: Sergei AkulichThe 10 Most Challenging Hikes in Connecticut
Connecticut's ten hardest hikes — expert difficulty, big mileage, or serious exposure. Reserved for experienced hikers.
Photo: Joshua EarleThe Best National Parks & Recreation Areas in Connecticut
Federal parks and recreation areas in Connecticut ranked by what they actually offer hikers and campers, not just popularity.
Photo: Tobias MrzykBest Waterfall Hikes in Connecticut: 10 Trails to See Falls Up Close
Connecticut's best hikes to named waterfalls — from short family-friendly viewpoints to all-day cascade chasing.