Windham County, Connecticut
154 hiking & walking trails · 2parks, recreation areas & campgrounds · 26 cities. Real OpenStreetMap + Recreation.gov data, with a free trail map for every listing.
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
Curated Guides for Windham County
Frequently Asked Questions
Are there hiking trails in Windham County, Connecticut?
Yes — we have 154 mapped hiking and walking trails in Windham County, Connecticut, sourced from OpenStreetMap. Browse the full list below, with distance, elevation, and difficulty for each.
What is the most difficult hiking trail in Windham County, Connecticut?
Sugar Brook Snowshoe Loop near Central Village is rated hard — the toughest classification among Windham County, Connecticut's mapped trails.
What is the best hiking trail in Windham County, Connecticut for families?
Agnes' Pasture Trail near Chaplin is one of the best family picks in Windham County, Connecticut — easy difficulty, short enough for kids and first-timers. See the full family hiking guide below for more options.
Is there a trail map for Windham County, Connecticut?
Each of the 154 trails in Windham County, Connecticut has its own page with an interactive map, GPS coordinates, and a link to view it on OpenStreetMap — no app or account needed.
What parks and recreation areas are in Windham County, Connecticut?
Windham County, Connecticut has 2 parks, recreation areas, and federal facilities in our index (1 classified as recreation areas). Each listing includes activities, photos where available, and directions.
Can I go camping in Windham County, Connecticut?
We don't show any campgrounds with mapped campsites in Windham County, Connecticut right now — check the state level for more camping options nearby.
Where can I find hiking trails and parks near Windham County, Connecticut?
Browse all hiking trails, walking trails, parks, and campgrounds across Connecticut for more options beyond Windham County, Connecticut.
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.