All Hiking Trails in Westchester County, Connecticut
719 trails across Westchester County. Search by trail name or city.
Page 1 of 15 (719 total)
From the OutsideAtlas Blog
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.