Windham County, Connecticut
154 hiking trails · 2parks & campgrounds · 26 cities. Real OpenStreetMap + Recreation.gov data.
About Hiking in Windham County, Connecticut
Windham County is home to 154 mapped hiking trails and 2 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 Windham County or browse parks. Want to narrow further? Pick a city below to see only that city’s outdoor options.
Trails & Parks in Windham County
Up to 156 pinpoints showing trail and park locations across the county.
Cities in Windham County
Click any city to see trails and parks within it.
2 more cities in this county.
Sample Parks in Windham County
Sample Trails in Windham County
Hiking guides for Connecticut
Statewide rankings and guides — useful context for Windham 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.